Stereochemical Aspects of the C -Glycosylation of Pyranosides and Furanosides.

Autor: Achanta, Srinivas, Sasikala, Ch. V. A., Basu, Debjit, Nahide, Pradip D., Bandichhor, Rakeshwar
Předmět:
Zdroj: Synthesis; Apr2024, Vol. 56 Issue 7, p1043-1069, 27p
Abstrakt: This document provides a comprehensive overview of the stereochemical aspects of C-glycosylation, focusing on the synthesis of glycoside-based drugs and the development of stereoselective methods for constructing C-glycoside bonds. It explores the conformational analysis of sugars and the role of Lewis acid-mediated nucleophilic addition in glycoside bond formation. The text also discusses various methods for the synthesis of C-glycosides, including Lewis acid mediated nucleophilic addition, arylalane addition, glucal epoxide method, glycosyl leaving group substitution method, and glycosylation via transition-metal-mediated cross-coupling. Additionally, the document discusses the stereochemistry of glycoside bond formation in furanosides and the influence of substituents on the stereochemical outcome. It concludes by summarizing the stereoselective synthesis of α- and β-C-glycosides and the factors that influence stereoselectivity. [Extracted from the article]
Databáze: Complementary Index