A practical method for the synthesis of sialyl alpha-glycosides

被引：62

作者：

Martichonok, V ^{[1
]}

Whitesides, GM ^{[1
]}

机构：

[1] HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1996年 / 118卷 / 35期

关键词：

D O I：

10.1021/ja960148b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Addition of 2,4-dimethylbenzenesulfenyl chloride to sialic acid glycal gives crystalline 2-chloro-3-thiosialic acid 3 in 85% yield. Reaction of 3 with sodium thiomethoxide in acetonitrile at 0 degrees C affords the sialic acid donor alpha-2-(methylthio)-3-thiosialic acid 4 in quantitative yield. Sialylation of glycosyl accepters 9 and 10 with 4 in the presence of phenylsulfenyl triflate (PST) as promotor in CH3CN at -40 degrees C gives alpha-sialosides in good yield and excellent stereoselectivity. No beta-sialosides are formed in either case. Removal of the auxiliary 3-(2,4-dimethylphenyl)-thio group is achieved in high yield using Ph(3)SnH and AIBN in refluxing toluene. Protected GM(3) trisaccharide and 6-sial-2-yllactose were obtained on a gram scale.

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页码：8187 / 8191

页数：5

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