2-(TRIMETHYLSILYL)ETHYL GLYCOSIDES - TRANSFORMATION INTO GLYCOPYRANOSYL CHLORIDES

被引：70

作者：

JANSSON, K

NOORI, G

MAGNUSSON, G

机构：

[1] LUND UNIV,LUND INST TECHNOL,CTR CHEM,BOX 124,S-22100 LUND,SWEDEN

[2] SYMBICOM AB,S-22370 LUND,SWEDEN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 10期

关键词：

D O I：

10.1021/jo00297a038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(Trimethylsilyl)ethyl (TMSET) glycosides were transformed in high yields into the corresponding 1-chloro sugars by treatment with 1,1-dichloromethyl methyl ether/zinc chloride. With acetyl, benzoyl, and benzyl protection of the 2-position, the a-glycopyranosyl chloride was the major product, whereas with the 2-phthalimido sugar 13, the β-chloride 21 was obtained. The fully benzylated TMSET glucopyranoside 1 gave the a-chloro sugar. 22 carrying a 6-0-formyl group whereas the partially benzylated sugars 16 and 17 gave the chloro sugars with all protecting groups intact. © 1990, American Chemical Society. All rights reserved.

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页码：3181 / 3185

页数：5

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