Evolution of a Reagent-Controlled Strategy for β-Selective C-Glycoside Synthesis

Abstract

C-Alkyl glycosides represent an attractive class of nonhydrolyzable carbohydrate mimetics which possess enormous potential as next-generation therapeutics. Methods for the direct stereoselective synthesis of C-alkyl glycosides with a broad substrate tolerance are limited, however. This is especially in the case of β-linked C-alkyl glycosides, where direct methods for synthesis from commonly available coupling partners remain limited. This Account describes the evolution of our laboratory’s studies on glycosyl sulfonate chemistry from a method for the construction of simple β-linked 2-deoxy-sugars to a technology for the direct synthesis of β-linked acyl and homoacyl glycosides that can be elaborated into more complex structures.

1 Introduction

2 Glycosyl Sulfonates

3 Glycosyl Sulfonates in Oligosaccharide Synthesis

4 Matching Donor and Sulfonate Reactivity

5 β-Linked C-Acyl and Homoacyl Glycoside Synthesis

6 Elaboration to other Products

7 Conclusion

Key words

glycosylation - C–C-bond-forming reactions - glycoconjugates - S_N2 reactions - reactivity

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