Concise synthesis of 1-deoxy-4-O-β-D-galactopyranosyl-D-nojirimycin avoiding a glycosylation step

被引：19

作者：

D'Andrea, F ^{[1
]}

Catelani, G ^{[1
]}

Mariani, M ^{[1
]}

Vecchi, B ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 06期

关键词：

1-deoxy-4-beta-D-galactopyranosyl-D-nojirimycin; aminocyclization; beta-D-galactopyranosyl-D-xylo-hexos-5-uloses; lactose;

D O I：

10.1016/S0040-4039(00)02165-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2',6'-Di-O-benzyl-2,3:5,6:3',4'-tri-O-isopropylidenelactose dimethyl acetal was used as starting material for the preparation of the until now unknown 4-O-beta -D-galactopyranosyl-D-xylo-hexos-5-ulose derivatives 7-9, through selective C-5 oxidation of its partially deprotected derivatives 4-6. Hydrolysis of 7-9 with aq. CF3COOH led to deprotected 1,5-dicarbonyl disaccharides 11-12, diastereoselectively transformed without purification into 1-deoxy-4-O-beta -D-galactopyranosyl-D-nojirimycin derivatives in about 60% yield, through a double reductive amination reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1139 / 1142

页数：4

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