Chapter 16. Synthesis of Enantiopure Azasugars from D-Mannitol: Carbohydrate and Peptide Mimics

  1. Yves Chapleur
  1. J.-C. Depezay

Published Online: 28 JAN 2005

DOI: 10.1002/3527603239.ch16

Carbohydrate Mimics: Concepts and Methods

Carbohydrate Mimics: Concepts and Methods

How to Cite

Depezay, J.-C. (2005) Synthesis of Enantiopure Azasugars from D-Mannitol: Carbohydrate and Peptide Mimics, in Carbohydrate Mimics: Concepts and Methods (ed Y. Chapleur), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527603239.ch16

Editor Information

  1. UMR CNRS 7565, Université Henri Poincaré-Nancy I, BP239, F-54506 Vandceuvre, France

Author Information

  1. Université René Descartes Paris V, Lab. Chimie et Biochimie Pharmacolique. et Toxicologiques, 45 Rue des Saints-Pères, 75270 Paris Cedex 06, France

Publication History

  1. Published Online: 28 JAN 2005
  2. Published Print: 12 NOV 1997

ISBN Information

Print ISBN: 9783527295265

Online ISBN: 9783527603237

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Keywords:

  • enantiopure;
  • azasugars;
  • D-mannitol;
  • carbohydrate;
  • peptide;
  • bis-aziridines;
  • azadisaccharides;
  • bis-epoxides;
  • somatostatin

Summary

  • Introduction

  • Results

    • To Azasugars via Bis-Aziridines

      • Nucleophilic Opening of Bis-Aziridines

      • Bis-Aziridines Precursors of Azadisaccharides

    • To Azasugars via Bis-Epoxides

      • Nucleophilic Opening of Bis-Epoxides

      • Isomerisation of Polyhydroxylated Piperidines

    • Isomerisation of Polyhydroxylated Azepanes

    • Inhibition Studies

    • Synthesis of Non-Peptide Mimics of Somatostatin

  • Conclusion

  • References