SYNTHESIS OF 1,4-ANHYDRO-2,3,6-TRI-O-BENZYL-ALPHA-D-GLUCOPYRANOSE BY CIS-RING-CLOSURE OF A GLYCOSYL CHLORIDE

被引：28

作者：

SATO, T ^{[1
]}

NAKAMURA, H ^{[1
]}

OHNO, Y ^{[1
]}

ENDO, T ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,RESOURCES UTILIZAT RES LAB,MIDORI KU,YOKOHAMA,KANAGAWA 227,JAPAN

来源：

CARBOHYDRATE RESEARCH | 1990年 / 199卷 / 01期

关键词：

D O I：

10.1016/0008-6215(90)84090-H

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：

A synthetic approach to 1,4-anhydro-2,3,6-tri-O-benzyl-a-d-glucopyranose by cis-ring closure of a glycosyl chloride has been studied to furnish a starting sugar for the synthesis of a linear (1→4)-linked polysaccharide. Cyclomaltoheptaose was benzylated and the product hydrolyzed to afford 2,3,6-tri-O-benzyl-a-d-glucopyranose, which was converted by HCl-Et2O into the corresponding glycosyl chloride. Treatment of the latter with NaH in Me2SO gave mainly 2-benzyloxy-3,6-di-O-benzyl-d-glucal, with 1,4-anhydro-2,3,6-tri-O-benzyl-a-d-glucopyranose as a byproduct. However, the 1,4-anhydro sugar could be prepared in good yield by cis ring-closure of 2,3,6-tri-O-benzyl-a-d-glucopyranosyl chloride in a mixture of tetrahydrofuran and sodium hydride. © 1990.

引用

页码：31 / 35

页数：5

共 7 条

[1] METHYL TERMINAL-4-0-METHYLMALTO-OLIGOSACCHARIDES [J].