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Keywords:

  • activated esters;
  • immunomodulatory glycans;
  • lacto-N-fucopentaose III (LNFPIII);
  • regioselective glycosylation;
  • oligosaccharides

Abstract

A concise synthetic route to an immunomodulatory pentasaccharide, lacto-N-fucopentaose III (1) and its corresponding human serum albumin conjugate, is described. Key transformations of the strategy include two highly regio- and stereoselective glycosylations for the construction of disaccharide 10 and pentasaccharide 12, a Birch reduction for deprotection of benzyl ethers, and a UV-promoted radical addition of a thiol to an alkene for modification of the aglycone.