SYNTHESIS AND NMR CHARACTERIZATION OF SOPHOROSYL TREHALOSE TETRASACCHARIDES

被引：11

作者：

WESSEL, HP

ENGLERT, G

机构：

[1] Pharma Division, Preclinical Research, F. Hoffmann-La Roche Ltd., CH-4002, Basel

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1994年 / 13卷 / 08期

关键词：

D O I：

10.1080/07328309408011856

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：

Glycosidation of 2',3',6'-tri-O-benzyl-alpha-D-glucopyranosyl 2,3-di-O-benzyl-4,6 4,6-O-benzylidene-alpha-D-glucopyranoside (2) with alpha-aceto-bromosophorose (1) gave the alpha- and beta-linked tetrasaccharides 3 and 4 in an approximately 2:1 ratio in dichloromethane or acetonitrile. The reaction is discussed, notably the predominant formation of alpha-glycosides. Both compounds were fully characterized by H-1 and C-13 NMR spectroscopy applying 1D TOCSY, 1D T-ROESY, H-1-detected one-bond and multiple bond H-1,C-13 2D COSY. Deprotection of 3 and 4 furnished the free sophorosyl trehaloses 7 and 8.

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页码：1145 / 1158

页数：14

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