Synthesis of 1-deoxy-D-galactohomonojirimycin via enantiomerically pure allenylstannanes

J Org Chem. 2004 Apr 2;69(7):2229-34. doi: 10.1021/jo0303012.

Abstract

1-Deoxy-D-galactohomonojirimycin was synthesized in seven steps from optically pure allenylstannane 4 and L-lactate-derived aldehyde 5 in 48% overall yield. The key step was the Lewis acid catalyzed reaction of 4 and 5 to give the syn-amino alcohol in excellent yield and very high diastereoselectivity.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • 1-Deoxynojirimycin / analogs & derivatives
  • Aldehydes / chemistry
  • Alkaloids / chemistry
  • Catalysis
  • Cyclization
  • Galactose / analogs & derivatives*
  • Galactose / chemical synthesis*
  • Galactose / chemistry
  • Indicators and Reagents
  • Lactic Acid / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Piperidines / analysis
  • Piperidines / chemical synthesis*
  • Stereoisomerism
  • Tin / chemistry*

Substances

  • 1-deoxy-D-galactohomonojirimycin
  • Aldehydes
  • Alkaloids
  • Indicators and Reagents
  • Organometallic Compounds
  • Piperidines
  • 1-Deoxynojirimycin
  • Lactic Acid
  • Tin
  • Galactose