2 SYNTHETIC ROUTES TO 2',3'-DIDEOXY-3'-C-(HYDROXYMETHYL)-4'-THIONUCLEOSIDES

被引：20

作者：

MANN, J ^{[1
]}

TENCH, AJ ^{[1
]}

WEYMOUTH, AC ^{[1
]}

SHAWPONTER, S ^{[1
]}

YOUNG, RJ ^{[1
]}

机构：

[1] WELLCOME RES LABS,DEPT MED CHEM,BECKENHAM BR3 3BS,KENT,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 06期

关键词：

D O I：

10.1039/p19950000677

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of 2',3'-dideoxy-3'-C-(hydroxymethyl)-4'-thionucleosides have been prepared from either (4R,5S)-4,5-bis(tert-butyldimethylsiloxymethyl)tetrahydrofuran-2-one or from (2R,3R)-1-benzyloxy-3(benzyloxymethyl)hex-5-en-2-ol. The former was converted into methyl (3R,4S)-4-acetylsulfanyl-5-(tert-butyldimethylsiloxy)-3-(tert-butyldimethylsiloxymethyl) and then into 1-0-acetyl-2,3-dideoxy-3-C- (tert-butyldimethylsiloxymethyl)-5-0-(tert-butyldimethylsilyl)-4-thio-D-evythro-pentofuranose prior to coupling with silylated pyrimidines. The second key intermediate was converted into (2R,3R)-1-benzyloxy-3-benzyloxymethyl-5,5-bis(benzylsulfanyl)pentan-2-ol and thence via the mesyl ester into 1-S-benzyl-5-0-benzyl-3-C-(benzyloxymethyl)-2,3-dideoxy-1,4-dithio-D-erythro-pentofuranose prior to coupling with silylated pyrimidines.

引用

页码：677 / 681

页数：5

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