Some amino sugars structurally related to 6-deoxymannojirimycin precursors prepared from methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose and methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside

Carbohydr Res. 2002 Apr 17;337(8):663-72. doi: 10.1016/s0008-6215(02)00058-7.

Abstract

Methyl (5S)-5-C-amino-5-cyano-5-deoxy-2,3-O-isopropylidene-alpha-D-lyxofuranoside has been synthesised from methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside, applying the Strecker synthesis. Analogously, methyl (5S) and (5R)-5-C-amino-5-cyano-5,6-dideoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosides were prepared from methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose. The 5-S configuration was unambiguously determined by single-crystal X-ray diffraction analysis of corresponding N-acetyl derivatives. Conformations of five-membered rings are discussed. The conversion of N-acetylated amino nitriles to N-acetylamino acid ethyl ester and amide, respectively, is also described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Deoxynojirimycin / analogs & derivatives
  • Amino Sugars / chemical synthesis*
  • Amino Sugars / chemistry
  • Carbohydrate Conformation
  • Crystallography, X-Ray
  • Disaccharides / chemistry*
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure
  • Nitriles
  • Pentoses / chemistry*
  • Rhamnose / analogs & derivatives*

Substances

  • 6-deoxymannojirimycin
  • Amino Sugars
  • Disaccharides
  • Nitriles
  • Pentoses
  • methyl 2,3-O-isopropylidene-pentodialdo-1,4-furanoside
  • methyl 6-deoxy-2,3-O-isopropylidene-hexofuranosid-5-ulose
  • 1-Deoxynojirimycin
  • Rhamnose