Synthesis of the saccharomicin fucose-aglycon conjugate and determination of absolute configuration

Org Lett. 2005 Oct 13;7(21):4749-52. doi: 10.1021/ol051971s.

Abstract

[reaction: see text] Schmidt glycosylation of the appropriately protected 3,4-dihydroxycinnamate methyl ester with 2,3,4-triacetoxyfucopyranosyltrichloroacetimidate gives aryl glycoside in high yield and diastereoselectivity. 2-Sulfation of fucose, installation of taurine, and global deprotection of the remaining protecting groups affords the fucose-aglycon conjugate of saccharomicin. This synthesis which arises from L-fucose also establishes the absolute configuration of the reducing terminus of the saccharomicin oligosaccharide.

Publication types

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

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Carbohydrate Conformation
  • Fucose / chemistry*
  • Glycosylation
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Stereoisomerism

Substances

  • Anti-Bacterial Agents
  • Oligosaccharides
  • Fucose