Chapter 10. Carbohydrates as Sources of Chiral Inositol Polyphosphates and Their Mimics

  1. Yves Chapleur
  1. D. J. Jenkins,
  2. A. M. Riley,
  3. B. V. L. Potter

Published Online: 28 JAN 2005

DOI: 10.1002/3527603239.ch10

Carbohydrate Mimics: Concepts and Methods

Carbohydrate Mimics: Concepts and Methods

How to Cite

Jenkins, D. J., Riley, A. M. and Potter, B. V. L. (2005) Carbohydrates as Sources of Chiral Inositol Polyphosphates and Their Mimics, in Carbohydrate Mimics: Concepts and Methods (ed Y. Chapleur), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527603239.ch10

Editor Information

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

Author Information

  1. Dept of Medicinal Chemistry, School of Pharm. and Pharmacol., University of Bath, Claverton Down, Bath, BA7AY, UK

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:

  • carbohydrates;
  • inositol polyphosphates;
  • D-2-deoxy-myo-inositol 1,3,4,5-tetrakisphosphate;
  • methyl 4,6-O-benzylidene-α-D-glucopyranoside;
  • Ins(1,4,5)P3

Summary

  • Introduction

  • Synthesis of D-2-deoxy-myo-inositol 1,3,4,5-tetrakisphosphate

    • Improved Preparation of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside and Methyl 4,6-O-Benzylidene-α-D-Mannopyranoside

    • Benzylation of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside and Related Reactions

    • Preparation of Methyl 3,4-Di-O-benzoyl-2-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranoside 30

    • Ferrier Carbocyclisation of 30

    • Attempted Inversion of Stereochemistry at Position 5 of 32

    • Synthesis of D-2-Deoxy-myo-inositol 1,3,4,5 Tetrakisphosphate 5

  • Synthesis of Ring-contracted Analogues of Ins(1,4,5)P3

    • Preparation of Methyl 2-O-Benzyl-3,4-di-O-(p-methoxybenzyl)-α-D-Glucopyranoside 58

    • Preparation of (1R,2R,3S,4R,5S)-3-Hydroxy-1,2,4-trisphospho-5-vinyl Cyclopentane 53b

    • Preparation of (1R,2R,3S,4R,5S)-3-Hydroxy-5-hydroxymethyl-1,2,4 trisphospho Cyclopentane 75

  • Synthesis of a Carbohydrate-based Inositol Polyphosphate Mimic Based on Adenophostin A

    • Synthesis of 2,6-Di-O-benzyl-3,4-di-O-(p-methoxybenzyl)-D-Glucopyranose 93

    • Synthesis of (2-Hydroxyethyl)-2′,3,4-Trisphosphate-α-D-Glucopyranoside 88

    • Preparation of a Fluorescent Label Based upon (2-Hydroxy-ethyl)-2′,3,4-trisphosphate-α-D-Glucopyranoside

  • Conclusion

  • References