Efficient dehydrative sialylation of C-4-aminated sialyl-hemiketal donors with Ph2SO/Tf2O

J Org Chem. 2009 Feb 20;74(4):1733-5. doi: 10.1021/jo802396a.

Abstract

An efficient approach to the dehydrative sialylation of various substrates with C-4-aminated sialyl-hemiketal donors by using the reagent combination of diphenyl sulfoxide and triflic anhydride is reported. By using a C-4-hindered non-nucleophilic amine auxiliary, excellent yields and high alpha-stereoselectivities were obtained for coupling with a wide range of primary and secondary acceptors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Amines / chemistry*
  • Benzene Derivatives / chemistry*
  • Mesylates / chemistry*
  • N-Acetylneuraminic Acid / chemistry*
  • Pyrimidines / chemistry
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Amines
  • Benzene Derivatives
  • Mesylates
  • Pyrimidines
  • diphenyl sulfoxide
  • N-Acetylneuraminic Acid
  • trifluoromethanesulfonic acid
  • pyrimidine