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DOI: 10.1055/a-1755-3090
Evolution of a Reagent-Controlled Strategy for β-Selective C-Glycoside Synthesis
We thank the National Science Foundation (CHE-1300334, CHE-1566233, and CHE-1954841) and the National Institutes of Health (NIH) common fund (U01-GM120414) for generously support this research program.
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
Publication History
Received: 21 January 2022
Accepted: 31 January 2022
Accepted Manuscript online:
31 January 2022
Article published online:
21 February 2022
© 2022. Thieme. All rights reserved
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