C-Glycopyranosyl aldehydes: emerging chiral synthons in organic synthesis

Authors

Sandeep Kumar, University of Delhi
Vinod Khatri, University of Delhi
Priyanka Mangla, University of Delhi
Rajni Johar Chhatwal, University of Delhi
Virinder S. Parmar, CUNY Medgar Evers CollegeFollow
Ashok K. Prasad, University of Delhi

Document Type

Article

Publication Date

2023

Abstract

Herein, we have summarized the vast array of synthetic processes that have been developed for the synthesis of C-glycopyranosyl aldehydes and diverse C-glycoconjugates derived from them by covering the literature reported from 1979 to 2023. Notwithstanding its challenging chemistry, C-glycosides are considered stable pharmacophores and are used as important bioactive molecules. The discussed synthetic methodologies to access C-glycopyranosyl aldehydes take advantage of seven key intermediates, viz. allene, thiazole, dithiane, cyanide, alkene, and nitromethane. Furthermore, the integration of complex C-glycoconjugates derived from varied C-glycopyranosyl aldehydes involves nucleophilic addition/substitution, reduction, condensation, oxidation, cyclo condensation, coupling, and Wittig reactions. In this review, we have categorized the synthesis of C-glycopyranosyl aldehydes and C-glycoconjugates on the basis of the methodology used for their synthesis and on types of C-glycoconjugates, respectively.

Comments

This article was originally published in RSC Advances, available at https://doi.org/10.1039/D3RA02122J

This work is published under a Creative Commons Attribution-NonCommercial 3.0 Unported License.