Coupling of Glycal Derived Thioethyl Glycosyl Donors with Glycal Acceptors. An Advance in the Scope of the Glycal Assembly

Peter H. Seeberger,*† Matthias Eckhardt,† Clare E. Gutteridge,‡ and Samuel J. Danishefsky*†‡
Contribution from the Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, and Department of Chemistry, Columbia University, Havemeyer Hall, New York, New York 10027
J. Am. Chem. Soc., 1997, 119 (42), pp 10064–10072
DOI: 10.1021/ja971640d
Publication Date (Web): October 22, 1997
Copyright © 1997 American Chemical Society

Abstract

Glycals were converted into thioethyl glycosyl donors through 1,2-anhydrosugar intermediates. Various participating groups in the C-2 position were examined for formation of β-glucosyl, β-galactosyl, and α-mannosyl linkages. A number of disaccharides was prepared employing a novel coupling protocol involving thioethyl 2-pivaloyl glycosyl donors and glycal acceptors. Using this methodology, a linear tetrasaccharide containing exclusively β-glucosyl-(1→4) linkages was prepared in high yields. Ready application to α-mannosylation and C2 branching are other hallmarks of the method.

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History

  • Published In Issue October 22, 1997
  • Received May 20, 1997

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