N-p-methoxybenzylidene derivatives of 2-amino-2-deoxy-D-glucose as glycosyl donors: a reinvestigation

Carbohydr Res. 1990 Apr 25:200:319-37. doi: 10.1016/0008-6215(90)84200-e.

Abstract

6-O-Acetyl-3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-D- glucopyranosyl chloride, 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-alpha-D-glu copyranosyl bromide, 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-alpha- and -beta-D- glucopyranosyl trichloroacetimidate, and 3,4,6-tri-O-acetyl-2-deoxy-2-p-nitrobenzylideneamino-alpha-D-gluco pyranosyl bromide have been synthesised, and their behaviour as glycosylation agents with various soluble promoters has been investigated. The results obtained question the accepted non-participating character of the N-p-methoxybenzylideneamino group.

MeSH terms

  • Benzylidene Compounds*
  • Carbohydrate Sequence
  • Chemical Phenomena
  • Chemistry
  • Glucosamine / analogs & derivatives*
  • Glycosylation
  • Methylation
  • Molecular Sequence Data

Substances

  • Benzylidene Compounds
  • Glucosamine