Chapter 4. Solid-Phase Oligosaccharide Synthesis

  1. Prof. Dr. Chi-Huey Wong
  1. Peter H. Seeberger

Published Online: 28 JAN 2005

DOI: 10.1002/3527602437.ch4

Book Title

Carbohydrate-Based Drug Discovery

Carbohydrate-Based Drug Discovery

Additional Information

How to Cite

Seeberger, P. H. (2005) Solid-Phase Oligosaccharide Synthesis, in Carbohydrate-Based Drug Discovery (ed C.-H. Wong), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527602437.ch4

Editor Information

  1. Ernest W. Hahn Chair in Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines RoadLa Jolla, CA 92037, USA

Publication History

  1. Published Online: 28 JAN 2005
  2. Published Print: 26 AUG 2003

ISBN Information

Print ISBN: 9783527306329

Online ISBN: 9783527602438

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CHAPTER TOOLS

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Keywords:

  • solid-phase oligosaccharide synthesis;
  • linkers

Summary

  • Introduction

  • Pioneering Efforts in Solid-Phase Oligosaccharide Synthesis

  • Synthetic Strategies

    • Immobilization of the Glycosyl Acceptor

    • Immobilization of the Glycosyl Donor

    • Bi-directional Strategy

  • Support Materials

    • Insoluble Supports

    • Soluble Supports

  • Linkers

    • Silyl Ethers

    • Acid- and Base-Labile Linkers

    • Thioglycoside Linkers

    • Linkers Cleaved by Oxidation

    • Photocleavable Linkers

    • Linkers Cleaved by Olefin Metathesis

  • Synthesis of Oligosaccharides on Solid Support by Use of Different Glycosylating Agents

    • 1,2-Anhydrosugars – The Glycal Assembly Approach

    • Glycosyl Sulfoxides

    • Glycosyl Trichloroacetimidates

    • Thioglycosides

    • Glycosyl Fluorides

    • n-Pentenyl Glycosides

    • Glycosyl Phosphates

  • Automated Solid-Phase Oligosaccharide Synthesis

    • Fundamental Considerations

    • Automated Synthesis with Glycosyl Trichloroacetimidates

    • Automated Synthesis with Glycosyl Phosphates

    • Automated Oligosaccharide Synthesis by Use of Different Glycosylating Agents

    • Cap-Tags to Suppress Deletion Sequences

    • Current State of the Art of Automated Synthesis

  • Conclusion and Outlook

  • References

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