Short and straightforward synthesis of (-)-1-deoxygalactonojirimycin.
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%.
Karjalainen
Oskari K
OK
Aalto University School of Science and Technology, Faculty of Chemistry and Materials Sciences, Department of Chemistry, P.O. Box 16100, FI-00076 Aalto, Finland.
Passiniemi
Mikko
M
Koskinen
Ari M P
AM
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D015394:Molecular Structure; D013237:Stereoisomerism
D017485:1-Deoxynojirimycin; C090092:migalastat; D006026:Glycoside Hydrolases