6-deoxy-allo-nojirimycin in the racemic and D-series, 6-deoxy-D,L-talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2-D,L-allosamine via hetero-Diels-Alder cycloadditions.

被引：28

作者：

Defoin, A

Sarazin, H

Streith, J

机构：

[1] Ecl. Natl. Sup. de Chim. de Mulhouse, Université de Haute Alsace, F-68093 Mulhouse Cédex, 3, rue Alfred Werner

来源：

TETRAHEDRON | 1997年 / 53卷 / 40期

关键词：

D O I：

10.1016/S0040-4020(97)00897-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder cycloaddition of hexadienal dimethylacetal 3 to achiral acylnitroso-dienophile 5a gave the racemic cycloadducts 7a-c and, to chiral chloronitroso-dienophile 6, enantiomerically pure D-10a as sole adduct. Simple chemical transformations led to 6-deoxy-2-D,L-allosamine 15b, to 6-deoxy-D,L and D-allo-nojirimycin 15a, D-15a, to 6-deoxy-D,L-talo-nojirimycin 15c as well as to their l-deoxy-derivatives 16a, D-16a, 16c via their crystalline l-deoxy-l-sulfonic acid derivatives (sulfite adducts). Amino-sugars 16a,c are mixtures of alpha- and -beta-anomers and of the corresponding imines. (C) 1997 Elsevier Science Ltd.

引用

页码：13769 / 13782

页数：14

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