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

Ondrej Simák; Jan Stanek; Jitka Moravcová

doi:10.1016/j.carres.2009.03.016

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

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

Authors

Ondrej Simák¹, Jan Stanek, Jitka Moravcová

Affiliation

¹ Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Prague, Czech Republic. simak@uochb.cas.cz

PMID: 19375073
DOI: 10.1016/j.carres.2009.03.016

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

1-Deoxynojirimycin / analogs & derivatives
1-Deoxynojirimycin / chemical synthesis*
1-Deoxynojirimycin / chemistry*
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism

Substances

Enzyme Inhibitors
1-Deoxynojirimycin
nojirimycin