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
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.
引用
收藏
页码:233 / 242
页数:10
相关论文
共 20 条