STUDIES OF THE STEREOSELECTIVE REDUCTION OF 2-HYDROXYIMINO-HEXOPYRANOSIDES - LIBH4-ME(3)SICL, A MILD REDUCING AGENT OF OXIMES TO AMINES

被引：22

作者：

BANASZEK, A

KARPIESIUK, W

机构：

[1] Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44

来源：

CARBOHYDRATE RESEARCH | 1994年 / 251卷

关键词：

D O I：

10.1016/0008-6215(94)84288-4

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Reduction of the title compounds of types 1 and 2 under mild conditions using LiBH4,-Me(3)SiCl species, followed by acetylation, yielded the corresponding 2-amino sugars of alpha-D-gluco (5) and beta-D-manno (6) configuration, respectively, with full stereoselectivity. Analogously, the beta-D-lyxo isomer of type 4 afforded the beta-D-talosamine 9 exclusively. The stereochemical outcome of the reduction of oximes of type 3 is controlled by the configuration of the substrate and the chemical features of the C-1-C-4 substituents, leading to ta[o (8) and/or galacto (7) isomers.

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页码：233 / 242

页数：10

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