2-BROMO-2-DEOXY SUGARS AS STARTING MATERIALS FOR THE SYNTHESIS OF ALPHA-GLYCOSIDE OR BETA-GLYCOSIDE OF 2-DEOXY SUGARS

被引：37

作者：

BOCK, K ^{[1
]}

LUNDT, I ^{[1
]}

PEDERSEN, C ^{[1
]}

机构：

[1] TECH UNIV DENMARK, DEPT ORGAN CHEM, DK-2800 LYNGBY, DENMARK

来源：

CARBOHYDRATE RESEARCH | 1984年 / 130卷 / JUL期

关键词：

D O I：

10.1016/0008-6215(84)85275-1

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：

3,4-Di-O-acetyl-2,6-dibromo-2,6-dideoxy-.alpha.-D-gluco- (1) and -D-mannopyranosyl bromide (18) gave, in glycosidation reactions, 1,2-trans-glycosides. .beta.-D-Glycosides were formed as the main products from 1 in moderate yields, whereas 18 gave .alpha.-D-glycosides exclusively and in high yields. The 2,6-dibromo-2,6-dideoxy-.beta.-D-glucosides were converted into the 2,6-dideoxy-.beta.-D-glycosides by treatment with tributylstannane, and removal of the Br atoms from 2,6-dibromo-2,6-dideoxy-.alpha.-D-mannosides to give 2,6-dideoxy-.alpha.-D-glycosides could also be effected by catalytic hydrogenolysis.

引用

页码：125 / 134

页数：10

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