Preparation of C-(2-deoxyhex/pent-1-enopyranosyl)heterocycles

Carbohydr Res. 1994 Feb 17:254:91-104. doi: 10.1016/0008-6215(94)84245-0.

Abstract

Acetylated 1-cyanoglycals (2,6-anhydro-3-deoxyhept/hex-2-enononitriles) were prepared by direct elimination of acetic acid from the appropriate acetylated 2,6-anhydrohept/hexononitriles with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in aprotic solvents. Heterocyclisation of the cyano group of acetylated 1-cyano-D-galactal with 2-aminothiophenol led to 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)benz othiazole. Several 2-(per-O-acetylhexo/pentopyranosyl)benzothiazoles also gave 2-(per-O-acetyl-2-deoxyhex/pent-1-enopyranosyl)benzothiazole s with DBU. 3-(Per-O-acetylhexo/pentopyranosyl)-[1,2,4]triazolo[4,3-a] pyrimidines rearranged with DBU to the corresponding acetylated 2-glycosyl-[1,2,4]triazolo[1,5-a]pyrimidines. By the reaction of 1-cyano-D-galactal with ammonium azide, 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)tetr azole was prepared and then transformed with carboxylic acid derivatives into 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)-5-s ubstituted-1,3,4- oxadiazoles.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyanides
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Optical Rotation
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / chemistry
  • Solvents
  • Stereoisomerism
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • Cyanides
  • Glycosides
  • Indicators and Reagents
  • Nucleosides
  • Oxadiazoles
  • Solvents
  • Thiazoles
  • Triazoles