Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker.

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.

SUBMITTER: Zhang J 

PROVIDER: S-EPMC3775522 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature