SYNTHESIS OF L-3'-AZIDO-3'-DEOXYTHYMIDINE AND ITS STEREOISOMERS

被引：46

作者：

WENGEL, J

LAU, J

PEDERSEN, EB

NIELSEN, CM

机构：

[1] ODENSE UNIV,DEPT CHEM,DK-5230 ODENSE,DENMARK

[2] STATENS SERUMINST,DEPT ENTEROVIRUS,RETROVIRUS LAB,DK-2300 COPENHAGEN,DENMARK

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 11期

关键词：

D O I：

10.1021/jo00011a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the first synthesis of the L isomer of 3'-azido-3'-deoxythymidine (L-AZT). L-Arabinose was used as starting material for preparation of appropriately protected alpha,beta-unsaturated aldehyde 5. Michael-type addition of azide to 5 gave 3-azido-2,3-dideoxypentofuranoses 7 and 8 suitable for nucleoside coupling with silylated thymine to afford after deprotection L-AZT (11), 1-(3-azido,-2,3-dideoxy-alpha-L-erythro-pentofuranosyl)thymine (12), 1-(3-azido-2,3-dideoxy-beta-L-threo-pentofuranosyl)thymine (13) and 1-(3-azido-2,3-dideoxy-alpha-L-threo-pento-furanosyl)thymine (14). Anti-HIV activity of L-AZT is discussed.

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页码：3591 / 3594

页数：4

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