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Chapitre D'ouvrage Année : 2019

N‐protecting Groups for 2‐Amino‐2‐deoxy‐glycosides

Résumé

2-Amino-2-deoxy-glycosides are representing a large portion of natural oligosaccharides, and the access to large quantities can be provided by robust and reliable synthetic strategies. The multiple chemical functionalities present on such saccharides such as aldehyde, hemiacetal, primary, and secondary alcohols, as well, of course, as the 2-amino moiety call for the design of orthogonal protecting group strategies capable of differentiating each position for the proper synthesis of the target molecules. This chapter will report the various amine protecting group strategies with the methods used for their introduction or removal as well as the influence on the glycosylation reaction or their stability under specific conditions. Interestingly, glycals have also been largely involved as precursors of 2-amino-2-deoxy-glycosides for powerful multistep total syntheses of large oligosaccharides.
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Dates et versions

hal-02325494 , version 1 (22-10-2019)

Identifiants

Citer

Sébastien Vidal. N‐protecting Groups for 2‐Amino‐2‐deoxy‐glycosides. Sébastien Vidal. Protecting Groups – Strategies and Applications in Carbohydrate Chemistry, Wiley, pp.169-200, 2019, 9783527340101. ⟨10.1002/9783527697014.ch6⟩. ⟨hal-02325494⟩
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