Stereodivergent De Novo Synthesis of Branched Amino Sugars by Lewis Acid Promoted Rearrangement of 1,2-Oxazines

被引：34

作者：

Pfrengle, Fabian ^{[1
]}

Lentz, Dieter ^{[1
]}

Reissig, Hans-Wrich ^{[1
]}

机构：

[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 17期

关键词：

amino sugars; carbohydrates; glycosylations; heterocycles; rearrangements; N-O BONDS; DIASTEREOSELECTIVE SYNTHESIS; LITHIATED METHOXYALLENE; TRISACCHARIDE MIMETICS; CONVENIENT SYNTHESIS; DERIVATIVES; INHIBITION; CLEAVAGE; NITRONES; CYCLOADDITION;

D O I：

10.1002/anie.200805724

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Well concealed: 1,2-oxazines such as 1 rearrange under Lewis acidic conditions to bicyclic products of type 2, which can be incorporated into oligosaccharides as protected amino sugar equivalents. Subsequent reductive steps provide unusual oligosaccharides 3 having C2-branched 4- amino sugar units. Most of the reactions proceed with excellent stereocontrol and allow the synthesis of a collection of stereoisomers. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3165 / 3169

页数：5

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