Short and Straightforward Synthesis of (−)-1-Deoxygalactonojirimycin

Short and Straightforward Synthesis of (−)-1-Deoxygalactonojirimycin

The mildness and low basicity of vinylzinc species functioning as a nucleophile in addition to α-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...

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Veröffentlicht in:Organic letters 2010-03, Vol.12 (6), p.1145-1147
Hauptverfasser: Karjalainen, Oskari K, Passiniemi, Mikko, Koskinen, Ari M. P
Format: Artikel
Sprache:eng
Schlagworte:
1-Deoxynojirimycin - analogs & derivatives
1-Deoxynojirimycin - chemical synthesis
1-Deoxynojirimycin - chemistry
Glycoside Hydrolases - antagonists & inhibitors
Molecular Structure
Stereoisomerism
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Beschreibung
Zusammenfassung:The mildness and low basicity of vinylzinc species functioning as a nucleophile in addition to α-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%.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100037c