THE USE OF N-ALKOXYCARBONYL DERIVATIVES OF 2-AMINO-2-DEOXY-D-GLUCOSE AS DONORS IN GLYCOSYLATION REACTIONS

被引：76

作者：

BOULLANGER, P

JOUINEAU, M

BOUAMMALI, B

LAFONT, D

DESCOTES, G

机构：

[1] Laboratoire de Chimie Organique II, C.N.R.S. U.A. 463, Université de Lyon I, F-69622 Villeurbanne, 43 Bd. du

来源：

CARBOHYDRATE RESEARCH | 1990年 / 202卷

关键词：

D O I：

10.1016/0008-6215(90)84077-8

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：

1,3,4,6-Tetra-O-acetyl-2-alkoxycarbonylamino-2-deoxy-β-d-glucopyranoses and 3,4,6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-a-d-glucopyranosyl bromides have been used as donors in glycosylation reactions with model alcohols. β-Glycosides were obtained in good yields and with a high degree of 1,2-trans stereoselectivity. An oxazolidinone was formed as the main product from the reaction of some of the glucopyranosyl bromides with alcohols of low reactivity, but the formation of all products could be interpreted by a strong participation of the alkoxycarbonylamino group. © 1990.

引用

页码：151 / 164

页数：14

共 50 条

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