“Wako Organic Square”Vol. 9(2002. 11)
Contents
1. pago TI 00000 06 0 00 DODO DO E Hun 3 lll ll 0 Il 0101010 gt G M OCO2Me MC Pd P P h3 Ph P CO2Me CH3CN rt 12h CO2Me MC Pd PPh3 PPh3 Yield Recovery 0 mo mo 15 2nd 3rd 4th 54 20 20 83 quant 90 quant 84 quant 94 quant 83 quant 0 0 No D ue p0000m000 209 15841 Triphenylphosphine Palladium Microencapsulated lg 11 1 09 11 als Kobayashi M Endo S Nagayama J Org Chem 63 6098 19980 9 Kobayashi T Ishida R Akiyama Org Lett 3 2649 200116 2 S Kobayashi S Nagayama J Am Chem Soc 120 2985 1998149 3 R Akiyama S Kobayashi Angew Chem Int Ed 18 40 20011 S candium Trifluoromethanesulfonate Microencapsulated 100 0 00000 0 0 0 000000 0 000 00 000000 0 00000000 00 1000000000 000000000 00000000 88 00 000000000000000 00000 000000 00000000000 poo N 00000 000000 0000000000000000 0000000 00000 00 8 Imino Aldol DO Flow System Run Yield 0 Ph 1 90 pd OSiMez NH 2 90 N MC OTA gt 88 Ph2. 111111 Horvathi Curra 11 1 U DO D tadil 0 U U 12 DUDU 0000 1 fluorous synthesis 0 000 121 tagd 000000 0 00000000000 OP Oye yah d 4 s 2 A xil ac LA mar PA 1 de La D cri i dev Ts anA u hu HE imini ia a mm il ehh de aw Ec 1 1 F p kur aam E DD SAS 800000 Ai n 000000 Li 0 0O tagi 0 11 111111 1111 1 111 UL 111 OO synthesis based on affinity separation 1 1 1 111 111 11111 1 1111 1 1 000000000000 000 5 2111 00 000000000000 0000000 LH 0000000 tagi U UU 000000000000 00000 0000000 TFA 1111 111 form 00000000 taqi 000000000000 UU 11 1 1 BO HUD 00 BOBEU 11111
3. B 0 1 0 0 OO 1111000 0 1 00 1 111 1 HEDD 000000 30 go 00000 II 0 TI Ii Hi Hi li ll HEHE TI HI IIIE E E EH H n Dod CH3 n Dod CH3 n Dod Nwe CH3 _ 040 28581 047 28591 T 040 28601 s 5 ME n Dod2CHB CH2 11 O CH3 E No 0e 040 28581 D Dodecyl Methyl Sulfide ugguue 1096 9 0006 047 28591 Dodecyl Methyl Sulfoxide ugguue 10g 18 0009 040 28601 f Dodecyldimethylsulfonium Iodide 10 14 000 Jd ov n RIT COOR2 ACO RI COOH 9 n Dod S Me n Dod S Me Y Me Bn Benzyl MOM Methoxymethyl 2 000 M R n Dod S Me NCS EGBN wern O O n Dod O Mg 2 1 OH NCS2N chlorosuccinimide Hl Org Lett 3 3128 2001 9 Tetrahedron Lett 42 9207 2001 X K Nishide S Ohsugi M Fudesaka S Kodama M Node Tetrahedron Lett 43 5177 20021 R2 Yield 91 99
4. 048 28401 88 amp 2 Difluoro 1 3 dimethylimidazolidine 13 000 O O O No l 9 l 0 ne nu unganmune 89 KPiethylaminosulfur Trifluoride DAST x m nthracene 9 10 bi 1 5 resorcinol 9 1 JA nthracene 9 10 big 5 resorcinol 1 1 U EL LIU LU HO OH 1 j HIHH HT 20024 20 000000000000000 ine DHOG m 0 00 0000000 00 00000 O O Diels A lderg IO HO d 5 II 111 11 1 00000000000 A 111 ZI O Bu 4 000000000000 1 1 BBIBIE DUDU nan gt lt ani 4n f 1 ue Ye EEE Zn 01 8040 0 00000000 0 d 0000000 00 Diels Alder y 5 CHO endo CHO O No 1 0e 0e 018 188516 1009 7 000 TE Anthracene 9 10 big 5 resorcinol 1100 4 ids 3060 11 K Kobayashi K Endo Y Aoyama H Masuda Tetrahedron Lett 34 7929 199319 ad Aoyama Y Imai K Kondo K Kobayashi Tetrahedron 51 348 1995 b Kondo T Sawaki M Koyanagi K Kobayashi H Masuda Y Aoyama J Am Chem Soc 117 8348 1995 3 K Rondo T Koike T Sawaki O Hayashida H M asu
5. 9 PEM MC OsOg 5mol 5 oH DHQD PPHAL 5mol 94149 9 o H20 aceton8 1 111 5 Ph KB FE CN H K2CO3 30 G 5h Rune 19 2 39 Yield of Produdt 854 664 849 e8 0 0 78 78 78 Recovery of Catalyst quant quant quant OR H3CH2C NG R OMe OR DHQD PHAL 0 O O Ne D 0 ne 00000 0 158 02411 Osmium Vlll oxide PEM Microencapsulated 0 0 20 000 1 1 S Kobayashi M Endo S Nagayama J Org Chem 63 6098 1998 2 S Kobayashi T Ishida R Akiyama Org Lett 3 2648 2001 1 TIT j T TT ue 0 08 1 111 VIII D000000M00D000 0000 0D 0000000000000 II UU ggggagaganaaauganaudgnganngagggggggggnaagagagannagannagaganagnaune 10 1 0300000 n n nnn n m DD D nin j D 000000 D D 1 0000 HT Aora PPhsgnunuuuuu HE Ei 0 IH Ti li li Hi li j li l ji li i i li IH j 111 0000004 1 1 JIH j ILI DODOD 11 d OD HI U U
6. DUDU DE 1111 WO 11 1 D 000000 21 HI 00 0 1 1 4 SU D 1 1 11 i DD DO D 1 111 1111 1 1 DO 1 00 BA NANA ANANA NANA BEE EU EOE C 111 ULL 1 1 i 111 DUDO 111 1 111 1 11 ENE L E E BL CB EE EL DO 1 1 1 1 1 1 111 1 1 DO 1111 11 01 1 ungue 1 5 Hinuma Y Habata R Fujii Y Kawamata
7. Li U 10009090000000 00 0000003 uli 8 000 1 l1 0100 0090015150 00000000000 imm Y CD ROMDOO00 O00 000000000 D0000000000 00000 06 0 CO ROMJDODO 0 n 000 ne 1 0 CD ROMH J SI 5 Base 00 000 000000000 Y E 10 000 0 0000 000 pe W men BFC0O402 db 9 513 compounds FC0402 sdf 9 Catalog viewer PAIAMO TOPES COMPAR 11 1 0 0 0000000 111 1 00000000000 1 1 111 0 M000 danterny III d DU J 1 DU SPOCII III HH 000 0 0000000000 0000000000000000000000000 00000000 06 A euuuiiauaumsiui 000000000000 O PANDHU 0 0 O 11 a08 000 0000 00 U O O O hydrophobid O O PS 19091 000 hydrophili n 00000 0000 ne 0006 E go0000000002090000000006 VEL e 2 0000 1 H IH li li 0000000000 PSH PAT 00000000000 I11 L nn n n X oPAJODONOF RAM BAL TRH HMP H i i e 1 0000000 1 ue nei nunnnnmanne EAD SK UJ PS SynPhase PS D series Lantern Starter Kit 000000000000 1900 94 00 S
8. H lj 04000000 vimm D 7E DAH DADO OO MODO EEE BEEBE 0000 111 1 1 1 11 1 1000 1 1 11 VITpPEMI IH HHH HI 0 00 0 000 00000 0000000 1 1 vimm 1 L 1 1 00000 KB Fg CNeTITI U H ll HIH li li li EE IE II Hi Hi li 2ii li li 80 0 00000 0 HI NH IT 0000 0 O O PEMOOL IT Phenoxyethoxymethyl polystyreng IHD 00000000 HI IIIIII DO 9 Hl IH 000000 0000000000006 OLS Aa EE Osmium VIll oxide PEM Microencapsulated P EM MC 4 LI LI LI LI LI Li 0000000000 DEI Kg F 2 li 0 1 uu 11 1 0 0000000000000000000 PEM polystyrene
9. 1 1 111 iit 1 1 1 1111111111 1 111111 1 1 1 11111 l DUDU TL 1111110 d DU Li LIL 11 ddp DD 111 00 0000000000000 1 Ll Li LI 111 S U 1 1 1 111 none uL DODO 0000000 11 BB 11111 BEN B 11 11111 NANA NANANG AH Li Ll 11 000 111111 uut 1 tag 111 11 1 11 U tag SAS D BED lJ U 900 U phase tag D 00 phase 000000000006 008800000 PECH tagd 000000000 000000000000 L 00 E 1 111 11111 11 1 111 11111 0000000000000 131 PECO I PEG 0000000 0 00 0 0400000000
10. 1 1 1 1 UU B 11 00 231000 Scaffold 00000 00000000 0000000000 H HHHH 000000 0000000000000 000060 111 0 080 0 Hl HH HHH 0000000000000 0000 ue JIH BB ID HD LL 01995 0000 0 0 120007 1 1 1 1 II LI IIJ TIT II HI Li 1 LJ 1 D 1 4074 000050710000 00000 000000000 0 0 0000000000000 14119 0000000000000 Merck Research Laboratories O O M00000 1 1 1 0000 III 211 1111111111 1 0004000 2000 UU optimization library L1 ED E D E 3 ugagag 0000000 0 009 4 1 3 a 5 e c A Ezi o p T 4 1 pri Jim 3 1 0 an o cyclin dependent kinasB CDKI T E 0000000
11. DIDI 1 11 DO O00000 00000000000000 0 oae 0000060 O O O No 0 ge 0 00 0 0 Ti 0 529 9529142 AVO X9Dichloremethylphenylsilane 1000 5 100 042 06441 M 109 4 5009 UICE D Diphenyldichlorosilane qum BOO 165 07542 2590 12 000 167 07541 10099 40 000 163 07141 199 5 600 169 071439 Palladium ll Acetate 504 21 0009 161 07142 2590 93 0009 192 01972 2590 1 2006 194 019719 Sodium Fluoride 10096 3 1006 196 01975 9 500g 7 300 DMF DHI B 1 000000000000 D 111 ooo aggaag 0 00 H 11 11 0000000000000 1 1 1 111 4 1 0000000900000 HGrignardl O0 0 00008 0000 TI 00 000 0000 000000 000009 tert BuMe2SiCI 1 5equiv imidazole 5equiv OTBS MeMgCI 2 2equiv OH OTBS 9 14 OH DMF rt THF CH3CN 49 HF CHO Lo e ar TN T Hu 100 38 h H N L G Quan J K Cha Synlett 1925 200110 O O O No ne ge unanumune 309 60121 1099 5 8006 305 601236 0 0 Butyldimethylchlorosilane gt 9 5099 22 5009 303 60124 10099 38 5009 082 03525 D Hydrofluoric Acid 6 500g 1 950 aH 111 11 1 00000 pu OH 0 48 Baylis B Mu
12. TNI msg iz 5 0 n 3 a is ern E H x 2 5 2 ROI exi s e D DH k a DM li 2 DH O oa a L 5 li a LU a L Ei E DE FETE ruil 2 7 1 F and meterocyclyl 2 F CH O R2 a Br HO xis aryl dialeylamina arviibio and 4 RI AN Pieterocyciylb and other R1 2 Hebaerocycle 1 Br F2 Arg haterocychy R CH CF Jani caes Exam pies T 3 F pm x k ar PR ET Bi 5862 paar um FI k rr mi um biis a 1 m a e um um t Wiki DI TN T m KEN Jamika Al sb P t di mi LA 1 pt TH iic mi ieri i noc Bd dH 814 Hi m MH _ lt lt xl M rar SEIT e Fat E A i L Y Mei E LES F H U LIN F i muri dana 8 21 44 054 O BBU 000000 110 0 0 0 00 0000 06 DADO DO Hi N HE TH TI 0000 14 5 pyrazolecarboxylic acids 1 pyrazolacetic acids 2 4 9 quinolinecarboxylic acids 3 4 oxo 14 dihydro 3 9 quinolinecarboxylic acids 4 pyrazolo 1 5 alpyrimidine 7carboxylic ac
13. 0 E Ex 0000 000000 000 400000060 100000 000000000 i j j j j i i Ii li 0 000 090000 H CU po0o0000000000 06 200000 gocooood000000000000000 mme 4100106 No n 06 NEW 019155479 Il Ii li li i 18 6 040 25507 pg00000000 4 1816 047 254976 00 i i l i 110009 1814 04332547709 Ii Ii Hi li 0 li 110009 18L6 209 13967 0QD00000000000000000 000000 18L6 208 134378 Il Ii j i li Ii i li li Hi li li l 000000 1814 205 13447 H Hi li li li 4 110009 18L 0000000000000 00000000 1 00 uL s i L 1 aui L L 32
14. DIDEN 0000 HTSIII 11111 III 111 ddp UD DD RTSH 1111111111 111111 1 1 M00000000 000000 111 1 1 1 DD 1 1 1 1 1 1111 0000 1 1 B II UUU 111 11111 II L 1 11 1 1 11 1 1 1 1 1 1 DADO DO l 111 n 1 9 E 1 Bd U ILI LI ll DUDU U DNA HH 0000000000000 U 1 1 LU orphan receptori 00080400000 LH DL CE 1 hGR30 00 00 prolactin releasing peptide
15. IIJ 00000 O OSchulta 269 3 0 0000000000000 CDK 0000000000 purvalnal BI O OO 00016106 Purvalnol AO O O O O 8 pPurvalnol AN 1 600 00 H j cell line GI 501 a 24 411 M 12 colon cancer NCI H522 non small cell lung cancer 1111 HB DU ult II z 8 8 E 1 Crea EL adn 5 EH 061 peg a D j P L DU 0 U D OC144 093 CDK 990000 000000060 0430000 Peer L 111111 1 1 BOO BED D 11 1 11 1110111111 9 11 111111 1 Badii idi 09000000000 Pop BED Ontogen 0 2451 Y D LIDD 0000000000 Pgp D 0 oci44 098 1 00 0 1 4 0931 N B 111 000000000 UDO 0000006 9 2 108000888 0 80 8088 0808080
16. AO Pa C WD mmm x AN mu np 41 T u Bs Jia a LU AT En di 1 tes 5 rers bum jt oam Y n g Sk 15 rr m La gt La L lt h mz Dm PAE mul e gt y OG O9 O rt 18 m x i E m um Y Xm L _ Pin iof in ng 1 ovo 3 11 i ag 1 ID Ji Y E n i T m n m m ILLI A ba Y L 1 L 1 11 LJ LJ 14 Ji LL 1J Bu n rm A L 11 O 33 dal Hi 17 ja Ti m EH mi dm m Q UB SE HE js Um 4 E E wa ES l LU gia Yu Ser her 23 T SC um a gt HL E aid 1 r TH A 1 r 5 1 1 E k IL kai Ww d an T EA 47 ar 82 at HE E a 88 DH Ar e x ES T m L E m nn BES mm Hi ek EAS x E 1 xwa i a H B b JA 1 mn 1 Cu ma az 8 ar 82 12 li li 1 0480 pt 0 000 M0 000 DODODO B B H N N B 1 1 II J 1 0000000 06 1 U drug likeJ0000000 0000000000 11 j UU 1
17. and S J T aylor J Chem Soc Perkin Trans 1 3815 2000 11 H T oy K D J anda Acc Chem Res 33 546 2000 12 Ando S Manabe Y Nakahara Y Ito Angew Chem Int Ed 40 4725 2001 13 T Horv th J R bai Science 266 72 1994 b I T 9 Horvath Acc Chem Res 31 641 1998 c D P Curran Angew Chem Int Ed Engl 37 1174 1998 9 1416 Luo Q Zhang Y Oderaoyoshi D P Curran Science 291 1766 2001 15 6 Zhang K Fukase and Kusumoto Tetrahedron Lett 40 7479 1999 9 16 6 Zhang K Fukase M Izumi Y Fukase and Kusumoto Synlett 590 2001 9 17 Y Fukase Zhang K Iseki M Oikawa K Fukase and S Kusumoto Synlett 1693 2001 n n n3 gs ge V J Chemical Diversity Labs 4000000 Y 0 11 111 11 1111 IIIIII IIIIII 000000000000 drug like O O Lipinski s rulg O O BE 11111 DO BOBO DO U 0 conformation 0 OU UD U DE D 1 1 1 HHH 000000000000 11 111 1 1 1 11 1 111111 LIT DUDU 000000
18. 0000 0000000000 11 1 Hillman li 00000000000 10000008 cuo H 30mol 301 As DMF r t 01300 910 M Shi K jiang C Q Li Tetrahedron Lett 43 127 20021 O O O No l ne mne 0 00 00 H 163 046019 o 9 199 1 3009 161 046029 Lj Proline 66 2599 5 2009 165 04605 5000 50 0009 132 061334 25m 2 0006 r m Pr G 136 06136 D EI OS 500ml 17 500 I j j Jj i l 0000000000000000 pn 090000 00 D 0000000000 1 00 000000000000000 R2oH MezNSO CI 2 0eq g coon29 000009000 00000000000000000000 RICOOH o Tg Orf 0000002000006 R3R4NH Cat DAMP 0 leq RICONR3RA K Wakasugi A Nakamura Y T anabe Tetrahedron Lett 42 7427 2001 0 No Ue 0000 09 046 262024 25ml 7 0006 Deyn Dimethylsulfamoyl Chloride e a su 204 02846 98096 Trimethylamine Solution 500ml 1 900 TAPIA PIAR A E m Tarma riri 150mg injection HHH O MODO Dd 00000000 000000000 000000000 06 000000000 00 1 2 00 HOOD OD O 000000 40000 ASI
19. 06 111 OOL 1 pg000900000000000 06 00000000000 1 111 06 000 1 DCD ROM TI 0000000000 0000000 Building Blocks Sp 5 0 5 IF LAB Ltd D 0 0 E 20907 EE DUDO O Smart Library of Small Molecules ummummungguuguugggugggggnguu nun 0 0000 600 0 000000000 0 0 0000 OA 0 000000000 00000000000 Stock 94 000 Viable 90000 00 01000 0 000 400M Hz Collection of Building Blocks NMRO LC 4 000000000 00 0 0 00 LA BI O O 2000 l 0 0 anapannuduue 000000 00 0 Quantity Standards and Formatting D U 11 500mg 0 1290 1 OU D CD UI 11 8 00 0000000000009 T Neosystem 00 00 0 li i li i li 000 HH 00000 0000000000 06 l Hi ii Ii IT Ii 0 0 Il IH ii Ii 0 0000000 EN li 000 00 000 000 0 0 06 dk 0000000000000000 000000 TI D00000000000000000000000 0000 06 li 000010 000009000 0 00000 000000000 ne Z I Q O S an
20. 1151 pego 1111 1 1 tag 1 L 11 00 1 1 111 00000000 Hamilton I D U D 0000000000000 160000000 Li TEED 1 1 11 JEN L 111 111 111 1 1 00 00 0 008 00 00 00009 111 do BAS 1 1 1 111 111 HEL 1 1 1 HENNE DADO 11111 0000000000000 AD SA SI 0000 080000 0001706 9 3000006 UU 1 1 1 1111111 1 1 iiL H HH 111111 11 1 1111 1 1 ID III HH 111 00000000000 111 DUDU 111 1 11111 HIH E EI
21. 300 Hl IH Hl Hl Hl HHHH li 00 000000000000000 L II IH LI DD LI 00 0 DUDU DULU 000000 HI Hi 0 RANTO DM D DODO i HH EE NO D0000 0000000004900 OO CHIRALPAKPASHI 000000000 0 00 00 00 1000000000000 00 HIJ CHIRALPAK9A S RHITI D 0000000000 20020 19000 CHIRALCELS OJ ROOO CHIRA LCEL 04180 IIJ 0 RAQOD Y 00 101101 HHHHHH 0 01000 HHH 0g 06 umuguugdgaggguuggugguge amp eunuggguuugue 1 1 0 00 00000000 11111 1 CUE E lI 81 1 0 201 000000000000000 000 1 11 1 1 CHIRALPAK ADJ AS 000000 T CHIRALCELS nn CHIRALPAKO CHIRALCELO gge nane nan uun9 ugue OJ H OJ RH 165 000 150 000 165 000 0 46cmp x 15cm Q46cmo x 25cm 0 40cmp x 1cm 30 sey 150 000 26 000 307 08521 305 08522 302 07971 26 000 309 08581 4 306 08231 4 26 000 26 0006 26 0009 306 0590 9 309 08601 305 08561 150 0006 300 08511 26 26 0009 308 08512 44305 07961 e 26 0009 p 30
22. M Hosoya 9 Fukusumi C Kitada Y Masuo T Asano H Matsumoto M 9 Sekiguchi T Kurokawa O Nishimura H Onda M Fujino Nature 393 272 1998 2 uuu 00000 000000 000000000 1000 000000 00000000 0 O 0 126 1997 0 3 S Mason M A Hermsmeier Curr Opin Chem Biol 3 342 1999 4 5 Borman Chem Eng News 78 53 2000 5 5 F Brady K Stauffer W C Lumma GM Smith H G Ramjit S D Lewis B J Lucas S J Gardell E A Lyle S D Appleby J Cook M A Holahan M T Stranieri J J Lynch jr Lin I W Chen K Vastag A M Naylor Olsen and J P Vacca J Med Chem 41 401 1998 9 6 N S Gray L Wodicka AM W H T hunnissen T C Norman S Kwon F H Espinoza D O Morgan G Barnes S LeClerc L Meijer S H Kim D J Lockhart and P G Schultz Science 281 533 1998 7 Zhang S Sarshar E J Moran S Krane J C Rodarte K D 9 Bentatoul R Dixon and A M N Mjalli Bioorg Med Chem Lett 9 10 2603 2000 9 84 TI 0 160 426 2002 989 00000000000 Deo 442 2002 10 S W Kaldor M G Siegel Curr Opin Chem Biol 1 1 1997 D S V Ley I R Baxendale R N Bream Jackson A G Leach D Longbottom M Nesi J S Scott R Storer
23. Yield 74 95 1a K Nishide S Ohsugi H Shiraki H T amakita M Node Y Y ano T Okonogi M Sunaga W T agaki J Chem Soc Chem Commun 922 1973 64 1 M Node K Kumar K Nishide S Ohsugi T Miyamoto 5al K Y amauchi Y Hisanaga M Kinoshita J Am Chem Soc 105 538 1983 20 5 1 1 00 0 0 0 00000 000 0 0000 057 2001114 5b K Y amauchi Y Hisanaga M Kinoshita J Chem Soc Perkin Trans 1 194 198311 0000000000 0000000 LI LI L 0 1 EEE OOOO Q gqQ _EoeQR Lo Q Qro yr qQD r pQoQ n yop zz nggOgEr gRK RKm o P_ I O DUO E ipnnumuugaggggguguauaugauuge 20000000000000 F H 1 TI Hi Hi HH HE 00 300000000006 HC Ca J 0000000000000 111 1 DALU lI 0000000000000 000000000 220405 40 30 Cs5HioF2N2 136 14 DAST 00000000 li Li ji HH Li 1 111 111 11111 HE 0000000004 m ma n C3n17 mn C8H17 0000000 97 396 000000000 PEA 92 8 0000000 e J O 0 No 1
24. Kobak D A Zolotarev LV Guro A S T rifilenkov and M Ugoleva J Combinat Chem 2002 Lee SA Long J H Murray J L Adams M E Nuttall 5 P Nadeau K Kikly J D Winkler C M Sung M D Ryan M A Levy P M Keller and W E DeWolf J Med Chem d4 2051 2002 000000000000000 0 HE 5 p Targ DUDUH 9 Wako Organic Square FAX 03 3270 8582 R 2 y pug p pua tm 7 1 2 1 3 R1 R2 H CH Ph 1 R3 H Alkyl Aryl Heteracyclyl and other R4 H Alkyl Aralkyl Aryl Heterocyclyi and other 2 RS H Alkyl 1 3 m 0 1 3 1 3 n 1 4 2 r 1 5 COCHA E nod NN asm fa TEM DAR p l nan DE 238 215 _ A ES AL TIT A bed Hb 273 5 47 DAMES al dm TE m DE x nol CO an 057 a 1888 raT dum THER R1 B2 Ug Ri Qe 3 1 3 R1 R22 H CH 1 R a H Akl Angl Hetirocydyl and ihar Rd EH Ally Pabrik and sihar 3 R5 H Ak 1 na1 4 2 3 1 3 1 3 R un e ii Es e a din ni B M s LA 5 4 v uH PaL EU c E DS 38 8 KELA ELM A mm k i A L F a KH a Nes 16 5 68 Tum dena ki 1 gr A 7
25. 00000 000004 1 1 O CL 0808 1 DUDU CDLH 0000000 0000 881 0o00 000000000 O 0000 0000 00 CL 0808 0 RI R2 1 1 0000000000000 UJU R302 0003 K 287 0599 K 284 2334 R302 0005 0000 UU O 111 1 U U DD D BB000000 060 CDL 400000000000 000000000000 TI U U BB V UII Idi Or al L V Prof A Ivachtchenko Dr Sc and l Okun Ph D Chemical Diversity Labs Inc USA 00000 000000000000000 ue 04000000000 O 20000 j DID 111100 00008000 ue BB R0521558 DU HIE 000000 0000 IK 751 0008 K 751 0017 K 751 0018 K 751 0027 K 751 0030 K 751 0031 B0022 0000000000000 1 88 0000000000 ue 10 agna BBO TIIIH Hi li li li 0009 ooo0g0000 080000000000 06 e aldehydes gt e amines secondary e ketones e amidoximes e carboxylic acids e alkylhalides e carboxylic acid halides e arylhalides e carboxylic acid esters 9 e nitril
26. 000000 0 ej j 0 0 00009 en HIHT HI 0 1 0 006 STORAGELIL 0000000000 gt http www orientalgiken co jp tatty T 111 1 1 j N Hi n i E A 0090 000808000 0 0 TI 0 TI 00 00 0010 ON PRTRI NGO 1 0 i li 0000 m Lu 000000 OLD ODO LJ L Lud EL ELELE EL EE EL ELE 0000000 Ll Li J LJ LI LJ LI L LI oO 0000000000 ep 0000000000000 UU Ll J E 10 LI LI L LI LIJ l HH HHHH O O O IM 7000 O 00006 URL Whttp www ishida co jp 0090 MARAE E e DI l JU inuuuune Ngka 1 0 00000000000000808000 0 18 1 0 0 0 0 000000 OTHFOD J l ji ji li HH li ji ji i 0 ji li DODO 0010 1
27. 000000 2400 000000000000 11 DO DADO DO 1 11 IIIIII 11100 000000000 0000000000060 0000000000 TIJI 000000000 LL 0000 1 1 1 1 11 71 41 1 11 0000 0000000000000 000 1 11 0000 00000000 00 0 000 ue Wako HDH 0 DOD00 00000 JIH II HI LI ILI LI 11111 III H HHHH LH 11 11 111111 DO IH IDI TIL 111 1 11 1 11111 Scaffold O 000 O 000 HIL 1 Scaffold 0 00 0 000 0 1 1111 DABA utl 1 11111 1
28. 09 111 1 11 11 1 1 1 1111 1 ID 1111 44000 tern 1 11 1 1 0 1111 PILI III uu 1111 1 1 DUYU 00 11 11 611 111 ODO EET EEE 1 1 L DOBO DDD 111 1 1 BILD UU 111 1 DO 1 111 1 1 1 BE BE DIUI 111111 1 1 1 111 11 1 111111 1 1 HH NNN EL TEED iib 00 IIIIII 000000 1 1 LEE 1 11111 11 000000 000000000 00 B 1 1 ND HL 111111 11
29. 2 302 08571 309 08221 9 0000000000 503 08241 lene x25cm 500 000 500 000 302 13221 303 13251 301 13311 xime 1 300 0006 gt 1 100 000 309 13231 300 13261 301 13291 308 13321 lcmpx2cm 150 000 150 000 150 000 150 000 000 0 00000 06 13241 307 13271 304 13301 305 13331 e D Bui 00000000 0000 0000 No O0000000000 0000000000000000 0000 ue JTU I 2 73 JL 1s bt T SR ik A AL b e j ILI N BD HH AZ 0000000000004 56000 A SP Active Server Pages T 1E LE E E 1 1 1 1 1 1 0000000000000 06 000000000000 00 1 00 0 06 0000 0000 li H TI DK NN N lu Li i A ALAA A li A A A NGA PRTRH li IH li Ii 1 li Ii 000 0 uugululilili Bib dH LIT LI EL ELE 000000000 DO 000000 06 PRT AH 00000000000 MSDS 0000 55 40000000 000000 0000006 ER STORAGE Il CMS 2000D 90000 000000000 9 9 j D000000000000 i1000 000 oo 0000 HIND ND 00 0000 0 00
30. 200 529 5207142 SPPSDHYP SynPhase PS D Series lyperlabile linker 1009 93 100 526 520819 SPPSLHYP _ SynPhase PS L Series Myperlabile linker 1009 54 200 526 824919 SPPSDBAL SynPhase PS D Series fBackbone Amide linker 1006 132 5009 529 82501 SPPSLBAL SynP hase PS L Series Backbone Amide linker 100 77 800 0000000000 PAHH 0000000000060 SPPALNOF00860 SynPhase PA D Series Non Functionalized gt 8u mole 1009 69 000 SPPADNOFO18 9 SynPhase PA D Series Non Functionalized 18u mole 1009 69 000 SPPALRAMO08 SynPhase PA D Series Rink Amide linker 8u mole 1009 93 0009 SPPADRAMO18 9 SynPhase PA D Series Rink Amide linker 18u mole 1009 93 000 SPPALHMPO008 9 SynPhase PA D Series Hydroxymethylphenoxy linker 8u mole 1009 93 000 SPPADHMPO018 9 SynPhase PA D Series Hydroxymethylphenoxy linker 18u mole 1006 93 000 SPPALTRHO08 9 SynPhase PA D Series Trityl Alcohol linker 8u mol 1006 93 0009 SPPADTRHO189 SynPhase PA D Series Trityl Alcohol linker 18u mole 1009 93 0009 SPPALHYPO08 9 SynPhase PA D Series Hyperlabile linker 8u mol 1006 93 0009 SPPADHYP01860 SynPhase PA D Series Hyperlabile linker 18u mole 1009 93 0009 SPPALBALOO8 SynPhase PA D Series Backbone Amide linker gt 8u mole 1009 132 500 SPPADBALO18 SynP hase PA D Series Backbone Amide linker 18u mol 100 132 500 ooa20g4g000000000000000 00000000000 9 0000000000 li 08000 000000000 li
31. KJ UJ PAD SynPhase PA D series Lantern Starter Kit O O00000 OM OOOO O 0 0 94 000 DIBI BDB TEB RAM O A o E TNH TFA salt Ba E o ES AMM CLM HYP OMe BAL TRH NOF O OMe 0 NH F Eo Qr E OH ES Moc OMe OMe H HHHHHHHHH 9 20000000 25 ji i D Series 3 mol L Series 15u mol 9 1 No nunmnu e 1 19 ne nunnummune 528 516039 SPPSDAMM SynPhase PS D Series 4 amp minomethylated 10060 66 9006 525 516139 SPPSLAMM SynPhase PS L Series fAminomethylated6 gt 1009 40 400 527 520119 SPPSDCLM 4 SynPhase PS D Series hloromethylated 1009 80 000 524 520219 SPPSLCLM SynPhase PS L Series hloromethylated 1009 47 200 506 460119 SPPSDHOM SynPhase PS D Series 4Mydroxymethylated 1009 80 000 503 460219 SPPSLHOM SynPhase PS L Series lydroxymethylated 1009 54 200 522 516239 SPPSDRAM SynPhase PS D Series ink Amide linker 1006 93 1009 529 516339 SPPSLRAM SynPhase PS L Series Rink Amide linker 1006 54 2009 522 824719 SPPSDHMP SynPhase PS D Series Hlydroxymethylphenoxy linker 1009 93 100 529 824819 SPPSLHMP SynPhase PS L Series Mydroxymethylphenoxy linker 1009 54 200 525 520519 SPPSDTRH 4 SynPhase PS D Series rityl Alcohol linker 1006 93 1009 522 520619 SPPSLTRH SynPhase PS L Series rityl Alcohol linker 1009 54
32. Ph 5 89 Ph H Ph 6 88 7 90 gununnnue AzaDiels Alder 0 D0000 00000000 31 00000 e Mannich DStrecher engnnunudggguunu O Michael 0 TI D O O HDiels Alder 0 No l l ne nungnmune 196 12041 Scandium Trifluoromethanesulfonate Microencapsulated 00000 lg 18 000 000 00000000067 8 199916 2 S Kobayashi Nagayama J Am Chem Soc 120 2988 199811 0000000000 Linked BINOL 2 BINOL 80000000000 BINOL DO D 1 D ELO D 1 0000 1 11 1 DUDU II J J 11100 00 0000 ue 11 1 00 CX AO OA LI OH HO OH HO OO UO Q7 X S S linked BINOL R R linked BINOL 1 110 0 0000 0 YA L O OMe III O 0 OMe 2R 3S syn compound yield up to 959649 dr up to syn anti 97 3 gt ee up to 99 OH 1mol 200000000 0 0 CO2Me R R La linked BINOL gt 10mol CO2Me CO2Me DME 4 C 85h 2 yield 96 CO2Me ee up to 99 0 O O No ge 0 00 00 3 3 Oxybis methylene lbis 1R 1 R 1 1 bi 2 naphthol gt 155 024219 200mo 25 000 R R l
33. S Shirakami Chem Lett 2627 20011 O O No o ge 0 01010 i Ti 0 527 500349 D 61 Buthy 3 methylimidazolium tetrafluoroborate 50ml 41 300 124 04811 D CAL A Thermostable 000 100Kunits gt 15 0006 121 048219 tipase CAL B 000 200Kunits 11 0009 224 00246 Vinyl acetate Monomer 6 500 1 260 4V l Hl li 000 0010 0 i IH 00 NH IH l li li li 0 00000000 00000000 RIOH 820 PP AG RIOR 1111 1 gt gt ZIN 74 97 H N H B N BIN B B H B B B B li 111 1 0000 0 170 HH Kobayashi S limura K Manabe Chem Lett 10 2002 O No e 0 0 0 0 0 TI E 017 1506542 inear Alkylbenzenesulfonic Acid DBSA PrG 500ml 2 600 059 02471 5ml 2 900 91 2 Ethanedithiol 057 02472 25ml 5 000 1 00000000000 00000 l 0000 DIHI NNN HIN HIDIN IB ex prasicoe Pd cat Campa un cusan M HUM RH EUM o ORION REG 1 T Huang CJ Li Tetrahedron Lett 43 408 20020
34. Wako No 9 No 9 NOVEMBER 2002 2002 qani 1000000000000000 1039 nini HEL ij DI DA HI N Ti DI N B EE HB o COLM DAS DRE e A OT 4070 EAS o TI NN NA qd SM 89 Neosystem 0 000 000 0000000000 8 E CD ROM 0000000000 4 86 Mimotopes 0 0 00 0101 0000 00000000 9 9 9 ida RH aap 9 1011 1 lt gt 0000 12 n 134 DD TUE e 139 149 A ao PO resen UE nen 149 sn O 154 NIN H HN DIDN E N TREE BR 159 1111711111 out ama D _ap 16017 0001010017 Pinus ewdi e va ay ren nv go dek benan a e 204 A 000000000 EN 189 eer t PR RIN 152524 19 JA A A A A E OUO 1 11 1 111 1 111 1 1 1 1 1 1 1 11 1 1 111 11111 iilii uui 111 BOBO 1 1000000000 1 11
35. da Y Aoyama J Am Chem Soc 119 4117 19974 4 a Sawaki Y Aoyama J Am Chem Soc 1214793 1999 14 b Sawaki T Dewa Y Aoyama J Am Chem Soc 120 8538 1998 Dewa Y Aoyama J Mol Catal A Chem 152 257 20001 Wittig 000000 DDDUDDDODDODDDDUDDODUDDe 40000000000 Wittigo B DI 00000 06 0000000000000000 ue 000000000000 DODO 11 000 Modo 1 000000 Horner Wittig 000 O uut 2247800000 0000000000 Horner Wittig D DU D D D U U Wittig Du 1 1 11 D0O00000000000000000000000000 0 000 00 00000 0 00 9 0 000 B 000 Homer witig O 00 000000 Ph2P O JCH2CF 39 CHO T 2eq 9 gt zi TBAF 10eq THF 97 13 TBAR tetrabutylammonium fluoride 0 0 0 IL Ti li ll li I Ii HEHE Ti HT Ii 00 00 Ii 0 000 0 ng Aldehyde Yield of Y 6 E Z Ratio phenyl 1b 68 2bJ 73220 p anisy 1627 78 204 9545 p chlorophenyl 1d 6 gt 78 24 824499 trans cinnanyl 162 8B 260 624289 2 indoly 176 78 219 100499 3 pyri
36. dyl 197 68 2976 73127 l InT Kobayashi T Eda O Tamura and H Ishibashi J Org Chem 67 3158 20021 O No 1 14 1 l 6 0 01000 III H 043 285714 199 4 5006 Diphenyl 2 2 2 trifluoroethyl phosphine Oxide 00000 049 28573 5g 12 000 GREEN CHEMISTRY 20020010 Ul N B B ue 111 0000000 MOOD 000000000 06 1 OB 1 1 1 BDB UU 0000000 11 ne imue 2000004 30000006 1 0 0 0 0 0 500 0 6 U 700 00 800000 i NS 11111 00000000000 m 1111111 1 ID ES e E E 00 00000000000 AU e 111111 L NE 000060 T Itoh E Akasaki K Kudo
37. es e hydrazines e sulfonyl halides e hydrazides e acrylamides e amines primary Template Description of the library Os e R1 Building Blocks UH R102 0003 K287 0599 Side Chains R1 Scafolds ved are seng CPT K284 2334 Example c mm H E w Y H H 5 5 1 y i p a 7 302 0005 Side Chains RZ HH iH TT 0 s J JA la L a 1 EL LM E n a s E ma Ps A vr a B 4 5 1 182 ENE FEA aE 3 3 hi J_l rum i b ilios a P M a pa e j bi k E X h in wi i 5 us cam n Pes an e ti nc LES MCN D pU m Heri KEJ WEN 8 33 0 1 MIJE N BIJ 7 J li y I P E 7 IT P j p e BER NO ie uon mi E mm gie m pu T E Em pH 8215 7 8 mi 8 22 m raz ar DH o ui 2 G j A d n gt i TE CH EN LEME 8 224 7 2 8 LE a g li m 8 9 1 a NL g gt Fa a E E z E ki i 1 52 CHE ioa m clin E E E ER d m Qm L E a E k H H
38. ids 5 0 000000 0 0000 0800000 BBJO U V V disubstituted ethylend propylenediamines 1 1 substituted 5 amino 3 9 methylpyrazoles 2 dialkylamines 3 LE E UU UU 0000000000 4 decahydroisoquinolines 5 234 9 9 tetrahydro 1H beta carbolines 600 0 0000 1 UU DOM 1 L3thiazolane4 carboxylic acids 2 2 3A49 tetrahydro 1H beta carboline 2carboxylic acids 3 alkyl 2 aminothiophene 3 carboxylates 4 alkyl 4 amino 2 thioxo 2 3 dihydro 1 3thiazole 5 carboxylates 5 60 8000 ne HHH 000000000 BBM 8009 un ne 11110 0000 ue 0006 000 00 100 000000000000 UU 11 1 UU 000 1900000 000 1 3 OP acrylamides propionamides B O0 O0 10 000000000000 0000000000 medicinal Chemistry 40 E 8000000000000 00 06 0 0120 2003000800800 8 B dimethylacrylamides 1 200 21 40 00 0 m 0 0 m0 un 41 550 0000 06 2 1 EL EH 0 0 0 0 0 POCA Lipinski Pharmacol Toxicol Methods 44 235 2002 Veber S R Johnson H Y Cheng B R Smith K W 3 Ward and K D Kopple J Med Chem 45 2615 2002 Ivachtchenko and V Kobak A bstracts of the 5th Annual Drug Discovery Conference T okyo J apan an V Ivachtchenko A P Il yin
39. inked BINOL 9 M e 3 3 Oxybis methylene bis 1S 1 S 1 1 bi 2 naphthol9 152 02431 200mg 25 000 S S linked BINOL uua 1 JN Kumagai S Matsunaga N Y oshikawa T Ohshima M Shibasaki Org Lett 3 1539 200119 20N Kumagai Matsunaga M Shibasaki Org Lett 3 4250 200119 3Y S Kim S Matsunaga J Das A Sekine Ohshima M Shibasaki J Am Chem Soc 122 6508 200011 Li U LH LL N HH HEL L HM EL BAN AH Bi LL DU I 1 1 Il ue 1 06 Li U Li Li 11 1 11 01111 0 01 Li Li pgmgggguununanuududggmnaggagadgguue 0 000 000000 0 0 0 0 0 0000 06 CT 24 mol96 ESTOS O O 77 O O O N NN 7 1 A 20 mol Pb OTf e eme Ph H2O iPrOH 1 4 5 0 C E Z lt 1 gt 99 Ph 99 yield syn anti 94 6 87 ee syn 023 14681 Binaphthyl 14 crown 4 1g 22 000 4023 1470 R 2P Binaphthyl 17 crown 5 1g 22 000 4027 4721 R 2 2 Binaphthyl 20 crown 6 19 2001 Bn Sos i 0 0 n 11 S Nagayama S Kobayashi J Am Chem Soc 122 11531 20001 Swern 00000 n1n 00000
Download Pdf Manuals
Related Search