Superarming common glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection

J Org Chem. 2010 Feb 19;75(4):1095-100. doi: 10.1021/jo9021474.

Abstract

A complementary concept for superarming glycosyl donors through the use of common protecting groups was previously discovered with S-benzoxazolyl (SBox) glycosyl donors. As this strategy can be of benefit to existing oligosaccharide methodologies, it has now been expanded to encompass a wide array of common, stable glycosyl donors. The versatility of this developed technique has been further illustrated in application to a sequential chemoselective oligosaccharide synthesis, wherein a superarmed ethyl thioglycoside was incorporated into the conventional armed-disarmed strategy.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Benzyl Compounds / chemistry*
  • Glycosylation
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Monosaccharides / chemistry*
  • Oligosaccharides / chemistry*
  • Stereoisomerism
  • Tissue Donors

Substances

  • Benzyl Compounds
  • Monosaccharides
  • Oligosaccharides