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

Author:

Bennett Clay S.

Abstract

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 Introduction2 Glycosyl Sulfonates3 Glycosyl Sulfonates in Oligosaccharide Synthesis4 Matching Donor and Sulfonate Reactivity5 β-Linked C-Acyl and Homoacyl Glycoside Synthesis6 Elaboration to other Products7 Conclusion

Funder

National Science Foundation

National Institute of General Medical Sciences

National Institutes of Health

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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