One-pot synthesis of oligosaccharides by combining reductive openings of benzylidene acetals and glycosylations

Org Lett. 2008 Aug 7;10(15):3247-50. doi: 10.1021/ol801076w. Epub 2008 Jun 26.

Abstract

Combining triflic acid-promoted glycosylations of trichloroacetimidates with reductive opening of benzylidene acetals with triflic acid and triethylsilane as one-pot procedures provides access to a wide range of disaccharides and 2,4- and 3,4-branched trisaccharides.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acetals / chemistry*
  • Benzylidene Compounds / chemistry*
  • Carbohydrate Sequence
  • Disaccharides / chemical synthesis
  • Glycosylation
  • Mesylates / chemistry
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Silanes / chemistry
  • Trisaccharides / chemical synthesis

Substances

  • Acetals
  • Benzylidene Compounds
  • Disaccharides
  • Mesylates
  • Oligosaccharides
  • Silanes
  • Trisaccharides
  • triethylsilane
  • trifluoromethanesulfonic acid