Reaktionen enolischer Zuckerderivate, XIV. Eine neue Synthese von L-Fucosamin durch „Azidonitratisierung︁ von L-Fucal

被引：19

作者：

Lehmann, Jochen ^{[2
]}

Reutter, Werner ^{[1
]}

Schöning, Dietgard ^{[1
]}

机构：

[1] Biochemisches Institut der Universität Freiburg, Hermann-Herder-Str. 7, Freiburg,D-7800, Germany

[2] Chemisches Laboratorium der Universität Freiburg, Albertstr. 21, Freiburg,D-7800, Germany

来源：

European Journal of Inorganic Chemistry | 1979年 / 112卷 / 04期

关键词：

Acid hydrolysis - Ammonolysis - Fucosamine - N acetyls - Sugar derivatives;

D O I：

10.1002/cber.19791120441

中图分类号：

学科分类号：

摘要：

Reactions of Enolic Sugar Derivatives, XIV. A New Synthesis of L-Fucosamine by „Azido-nitration︁ of L-Fucal. Starting from 3,4-di-O-acetyl-L-fucal (2) 3,4-di-O-acetyl-2-azido-2-deoxy-α-L-fucopyranosyl nitrate (3) was prepared by azido-nitration. Ammonolysis and reacetylation led to 1–N,3,4-O-triacetyl-2-azido-2-deoxy-α-L-fucopyranosylamine (4). De-O-acetylated 4 (5) was hydrogenized to yield crude l-N-acetyl-2-amino-2-deoxy-α-L-fucopyranosylamine which after acid hydrolysis yielded L-fucosamine (1). Copyright © 1979 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1470 / 1472