A general route to pendant C-glycosyl 1,2- and 1,3-diamines

Carbohydr Res. 2008 Apr 7;343(5):941-50. doi: 10.1016/j.carres.2008.01.030. Epub 2008 Feb 2.

Abstract

Practical and convenient preparations of C-glycosyl 1,2- and 1,3-alkanediamines are described. Two 1,2-ethylenediamine derivatives were synthesized from acetylated allyl alpha-C-glycosyl compounds via dibromination, azidation, carbohydrate deprotection, and azide reduction. Four 1,3-propanediamine derivatives were prepared from acetylated sugar halides via C-glycosylation with sodiomalononitrile, followed by the reduction of the nitrile moieties and the deacetylation of the carbohydrate moiety. These 1,3-propanediamine derivatives have the beta-anomeric configurations. The methods reported here serve as general routes to access carbohydrate-diamine conjugates with C-glycosyl linkages.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Crystallography, X-Ray
  • Diamines / chemical synthesis*
  • Diamines / chemistry
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Models, Molecular
  • Molecular Structure

Substances

  • Diamines
  • Glycosides