Chapter

Reactivity Tuning in Oligosaccharide Assembly

Volume 301 of the series Topics in Current Chemistry pp 141-188

Date:

Influence of Protecting Groups on the Reactivity and Selectivity of Glycosylation: Chemistry of the 4,6-O-Benzylidene Protected Mannopyranosyl Donors and Related Species

  • Sylvain AubryAffiliated withCentre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS
  • , Kaname SasakiAffiliated withCentre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS
  • , Indrajeet SharmaAffiliated withDepartment of Chemistry, Wayne State University
  • , David CrichAffiliated withCentre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRSDepartment of Chemistry, Wayne State University Email author 

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Abstract

The genesis and development of the 4,6-O-benzylidene acetal method for the preparation of β-mannopyranosides are reviewed. Particular emphasis is placed on the influence of the various protecting groups on stereoselectivity and these effects are interpreted in the framework of a general mechanistic scheme invoking a series of solvent-separated and contact ion pairs in dynamic equilibrium with a covalent α-glycosyl trifluoromethanesulfonate.

Keywords

Acetal Anomeric effect Diastereoselectivity Glycosylation Ion pair Kinetic isotope effect Stereoelectronic effects