Odorless Access to Thioglycosides for Oligosaccharide Synthesis: Their Design and Advanced Procedures for Thioglycosidation

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  • Dohi Hirofumi
    Division of Nanobiology, Graduate School of Advanced Integration Science, Chiba University
  • Nishida Yoshihiro
    Division of Nanobiology, Graduate School of Advanced Integration Science, Chiba University

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  • 糖鎖合成に向けた不快臭を伴わないチオグリコシドの利用：分子設計とチオグリコシド化法の進歩

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Abstract

Thioglycosides are widely used in the synthesis of oligosaccharides because they provide high levels of chemical stability and can be chemoselectively activated in a glycosylation reaction. Thioglycosides, however, are prepared from thiols, which can be challenging to use because of their pungent and generally unpleasant odors, as well as their tendency to form disulfides through oxidation, and these factors have effectively limited the application of thioglycosides in organic synthesis. Herein, we describe recent efforts towards the development of odorless methods for the preparation of thioglycosides, as well as an evaluation of their reactivity in the synthesis of oligosaccharides.

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