Synthesis of α-GalNAc thioconjugates from an α-GalNAc mercaptan

被引：71

作者：

Knapp, S ^{[1
]}

Myers, DS ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 09期

关键词：

D O I：

10.1021/jo0110909

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of functionalized thioglycosides and other derivatives (10-24) of 2-acetamido-2-deoxy-1-thio-alpha-D-galactopyranose have been prepared in good yields and with high anomeric purities by S-substitution reactions of the sulfide anion or sulfur-centered radical from mercaptan 6. Given the importance in nature of the alpha-GalNAc 1-O-linkage, and the greater chemical and biological stability of the corresponding 1-S-linkage, these thioconjugates may find application in studies of synthetic vaccines, enzyme inhibitors, glycomimetic scaffolds, and other complex carbohydrate systems.

引用

页码：2995 / 2999

页数：5

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