Thiosugars.: Part 1.: Preparation, structural elucidation and reactions of benzyl 2-deoxy-3,5-di-O-methyl-1,4-dithio-L-threo-pentofuranoside and synthesis of the corresponding 2′-deoxy-4′-thionucleosides

被引：14

作者：

Birk, C ^{[1
]}

Voss, J ^{[1
]}

Wirsching, J ^{[1
]}

机构：

[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany

来源：

CARBOHYDRATE RESEARCH | 1997年 / 304卷 / 3-4期

关键词：

2-deoxy-1,4-dithio-L-threo-pentofuranosides; 2-deoxy-4 '-thio-L-threo-nucleosides; configuration absolute; NOE-measurements;

D O I：

10.1016/S0008-6215(97)00233-4

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Benzyl 2-deoxy-3,5-di-O-methyl-1,4-dithio-L-threo-pentofuranoside (5) is synthesized in five steps starting with 2-deoxy-D-ribose. The anomers 5 alpha and 5 beta are separated and their configuration is unequivocally assigned by use of NOE measurements. 2-Deoxy-3,5-di-O-methyl-4-thio-L-threo-pentofuranose is obtained from 5 and mercuric 4-nitrobenzoate. The corresponding nucleosides are prepared from 5 and bis-(trimethylsilyl)uracil or bis-(trimethylsilyl)thymine in the presence of N-iodosuccinimide. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：239 / 247

页数：9

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