Synthesis of a new stable conformationally constrained 2,7-anhydrosialic acid derivative

J Org Chem. 2003 Nov 28;68(24):9528-31. doi: 10.1021/jo034679b.

Abstract

A stereoseletive synthesis of 2,7-anhydrosialic acid derivative 18 was achieved from d-glucono-delta-lactone. A highly syn-selective addition of Grignard reagent to theN-benzylimine 8 served as a key step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Gluconates / chemistry
  • Lactones / chemistry*
  • Models, Chemical
  • Molecular Conformation
  • Molecular Structure
  • N-Acetylneuraminic Acid / analogs & derivatives*
  • N-Acetylneuraminic Acid / chemical synthesis*
  • N-Acetylneuraminic Acid / chemistry
  • Stereoisomerism

Substances

  • Gluconates
  • Lactones
  • glucono-1,4-lactone
  • N-Acetylneuraminic Acid