A new route to aminosugars from sugar nitrones: synthesis of 6-deoxynojirimycin

被引：45

作者：

Dhavale, DD

Desai, VN

Sindkhedkar, MD

Mali, RS

Castellari, C

Trombini, C

机构：

[1] UNIV PUNE,DEPT CHEM,GARWARE RES CTR,PUNE 411007,MAHARASHTRA,INDIA

[2] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,I-40126 BOLOGNA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(97)00147-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The 1,3-addition of methylmagnesium chloride to dialdose derived nitrones 3 and 7 afforded N-benzylhydroxylamines 4/5 and 8/9, respectively, in high yields. The stereoselectivity of the addition reaction was improved by the use of trimethylsilyl triflate. The N-O bond reductive cleavages of N-benzylhydroxylamines took place in good yields and offered an easy access to N-benzylaminosugars. The potential of these aminosugars is demonstrated by the synthesis of glycosidase inhibitor 6-deoxynojirimycin 1a. (C) 1997 Elsevier Science Ltd.

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页码：1475 / 1486

页数：12

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