An efficient route toward 2-amino-beta-D-galacto- and -glucopyranosides via stereoselective Michael-type addition of 2-nitroglycals

Weihua Xue; Jiansong Sun; Biao Yu

doi:10.1021/jo900609s

An efficient route toward 2-amino-beta-D-galacto- and -glucopyranosides via stereoselective Michael-type addition of 2-nitroglycals

J Org Chem. 2009 Jul 17;74(14):5079-82. doi: 10.1021/jo900609s.

Authors

Weihua Xue¹, Jiansong Sun, Biao Yu

Affiliation

¹ State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.

PMID: 19453154
DOI: 10.1021/jo900609s

Abstract

Under the catalysis of DMAP or PPY in CH(2)Cl(2), the Michael-type addition of nucleophiles to 2-nitrogalactal or 2-nitroglucal leads in excellent yields and stereoselectivity to the corresponding beta-galacto- or -glucopyranosides, which are ready precursors to the biologically significant beta-d-galactosamine and -glucosamine units.

Publication types

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

MeSH terms

Catalysis
Combinatorial Chemistry Techniques
Glucosides / chemical synthesis
Glucosides / chemistry*
Glycosylation
Molecular Structure
Pyrans / chemistry*
Stereoisomerism

Substances

Glucosides
Pyrans