Short and straightforward synthesis of (-)-1-deoxygalactonojirimycin

Oskari K Karjalainen; Mikko Passiniemi; Ari M P Koskinen

doi:10.1021/ol100037c

Short and straightforward synthesis of (-)-1-deoxygalactonojirimycin

Org Lett. 2010 Mar 19;12(6):1145-7. doi: 10.1021/ol100037c.

Authors

Oskari K Karjalainen¹, Mikko Passiniemi, Ari M P Koskinen

Affiliation

¹ Aalto University School of Science and Technology, Faculty of Chemistry and Materials Sciences, Department of Chemistry, P.O. Box 16100, FI-00076 Aalto, Finland.

PMID: 20170191
DOI: 10.1021/ol100037c

Abstract

The mildness and low basicity of vinylzinc species functioning as a nucleophile in addition to alpha-chiral aldehydes is characterized by lack of epimerization of the vulnerable stereogenic center. This is demonstrated by a highly diastereoselective synthesis of 1-deoxygalactonojirimycin in eight steps from commercial starting materials with overall yield of 35%.

Publication types

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

MeSH terms

1-Deoxynojirimycin / analogs & derivatives*
1-Deoxynojirimycin / chemical synthesis
1-Deoxynojirimycin / chemistry
Glycoside Hydrolases / antagonists & inhibitors
Molecular Structure
Stereoisomerism

Substances

1-Deoxynojirimycin
migalastat
Glycoside Hydrolases