Double reductive amination of L-arabino-hexos-5-uloses: A diastereoselective approach to 1-deoxy-D-galactostatin derivatives

被引：39

作者：

Barili, PL ^{[1
]}

Berti, G ^{[1
]}

Catelani, G ^{[1
]}

DAndrea, F ^{[1
]}

DeRensis, F ^{[1
]}

Puccioni, L ^{[1
]}

机构：

[1] UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,I-56126 PISA,ITALY

来源：

TETRAHEDRON | 1997年 / 53卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(97)00063-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The double reductive amination of L-arabino-hexos-5-ulose with benzhydrylamine and NaBH3CN takes place in a diastereospecific manner giving in moderate chemical yield (36%) the galactosidase inhibitor 1-deoxy-D-galactostatin. The aminocyclization of 2,6-di-O-benzyl-L-arabino-hexos-5-ulose is more complicated giving results dependent from the type of amine: with ammonia or methylamine a mixture of C-5 epimeric 1-deoxyazapyranoses (D-galacto/L-altro ratio approximate to 4:1) is obtained in 45-65% combined yield, while with benzhydrylamine substantial amounts of an acyclic 1-deoxyl-benzydrylamino-hexitol (10% yield) is isolated together with the expected 1-deoxy-azasugars of the D-galacto and L-altro series. (C) 1997 Elsevier Science Ltd.

引用

页码：3407 / 3416

页数：10

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