2-(TERT-BUTYLDIMETHYLSILOXY)THIOPHENE - APPLICATION TO TOTAL SYNTHESES OF BOTH ENANTIOMERS OF 2',3'-DIDEOXY-4'-THIOCYTIDINE

被引:26
作者
RASSU, G [1 ]
SPANU, P [1 ]
PINNA, L [1 ]
ZANARDI, F [1 ]
CASIRAGHI, G [1 ]
机构
[1] CNR,IST APPLICAZ TECN CHIM,I-07100 SASSARI,ITALY
关键词
D O I
10.1016/0040-4039(95)00162-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Exploiting novel 2-(tert-butyldimethylsiloxy)thiophene (1, TBSOT) as versatile carbon nucleophile and both enantiomers of glyceraldehyde acetonide as chiral sources, an entry to both enantiomers of anti HIV-active 2',3'-dideoxy-4'-thiocytidine 10 and ent-10 was devised and executed.
引用
收藏
页码:1941 / 1944
页数:4
相关论文
共 20 条
[1]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 4'-THIO ANALOGS OF ANTIBIOTIC TOYOCAMYCIN [J].
BOBEK, M ;
BLOCH, A ;
WHISTLER, RL .
JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (02) :168-&
[2]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 5-FLUORO-4'-THIOURIDINE AND SOME RELATED NUCLEOSIDES [J].
BOBEK, M ;
BLOCH, A ;
PARTHASARATHY, R ;
WHISTLER, RL .
JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (08) :784-787
[3]  
BRANALT J, 1994, J ORG CHEM, V59, P4430
[4]  
BRANALT J, 1994, J ORG CHEM, V59, P1783
[5]   TOTAL SYNTHESIS OF (+)-2,8,8A-TRI-EPI-SWAINSONINE AND (-)-1-EPI-SWAINSONINE [J].
CASIRAGHI, G ;
RASSU, G ;
SPANU, P ;
PINNA, L ;
ULGHERI, F .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3397-3400
[6]   TOTAL SYNTHESIS OF 6-DEOXY-6-AMINOHEPTOPYRANURONIC ACID-DERIVATIVES [J].
CASIRAGHI, G ;
COLOMBO, L ;
RASSU, G ;
SPANU, P .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6523-6527
[7]   SELECTIVE REACTIONS USING N-(TERT-BUTOXYCARBONYL)-2-(TERT-BUTYLDIMETHYLSILOXY)PYRROLE - CONCISE ASYMMETRIC SYNTHESES OF (+)-1-DEOXY-8-EPI-CASTANOSPERMINE AND ITS ENANTIOMER [J].
CASIRAGHI, G ;
ULGHERI, F ;
SPANU, P ;
RASSU, G ;
PINNA, L ;
FAVA, GG ;
FERRARI, MB ;
PELOSI, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (23) :2991-2997
[8]   ASCENT OF THE ALDOSE SERIES BY 4 CARBON-ATOMS - TOTAL SYNTHESIS OF D-GLYCERO-D-TALO-L-TALO-UNDECOSE PENTAACETONIDE [J].
CASIRAGHI, G ;
COLOMBO, L ;
RASSU, G ;
SPANU, P .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2135-2139
[9]   THE 4-CARBON ELONGATION OF ALDEHYDO SUGARS USING 2-(TRIMETHYLSILOXY)-FURAN - A BUTENOLIDE ROUTE TO HIGHER MONOSACCHARIDES [J].
CASIRAGHI, G ;
COLOMBO, L ;
RASSU, G ;
SPANU, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2565-2567
[10]   N-(TERT-BUTOXYCARBONYL)-2-(TERT-BUTYLDIMETHYLSILOXY)PYRROLE - A PROMISING COMPOUND FOR SYNTHESIS OF CHIRAL NONRACEMIC HYDROXYLATED PYRROLIDINE DERIVATIVES [J].
CASIRAGHI, G ;
RASSU, G ;
SPANU, P ;
PINNA, L .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3760-3763