3-乙酰氨基-1,3,5-三脱氧-和1,3,5,6-四脱氧-1,5-亚氨基-D-葡萄糖醇的立体控制合成。

A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-D-glucitol.

作者信息

Simák Ondrej, Stanek Jan, Moravcová Jitka

机构信息

Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Prague, Czech Republic.

出版信息

Carbohydr Res. 2009 May 26;344(8):966-71. doi: 10.1016/j.carres.2009.03.016. Epub 2009 Mar 21.

DOI:10.1016/j.carres.2009.03.016

PMID:19375073

Abstract

3-acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-D-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-beta-D-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale.

摘要

3-乙酰氨基-5-氨基-3,5,6-三脱氧-D-葡萄糖-1,5-内酰胺和3-乙酰氨基-5-氨基-3,5-二脱氧-D-葡萄糖-1,5-内酰胺分别由相应的3-乙酰氨基-3-脱氧-β-D-吡喃葡萄糖苷合成，总产率分别为63%和35%。乙酰化后还原得到脱氧野尻霉素和1,6-二脱氧野尻霉素的标题化合物3-乙酰氨基-3-脱氧衍生物。所开发的方法适用于多克规模。