MilliporeSigma
  • Home
  • Search Results
  • Asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin via a ring-expansion approach.

Asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin via a ring-expansion approach.

Organic letters (2013-04-11)
Stephen G Davies, Aude L A Figuccia, Ai M Fletcher, Paul M Roberts, James E Thomson
ABSTRACT

The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-Deoxynojirimycin hydrochloride