Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement

A simple and environment-friendly citric acid-mediated synthesis of glycosides has been reported using Ferrier-rearrangement. Using this protocol, synthesis of several glycosides including pseudo disaccharides was prepared. Citric acid was successfully employed for the synthesis of glycosides from D...

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Bibliographic Details
Main Authors: P.I. Ramesh, Mohamad Saif Ali, Subhash Ghosh, Madhu Babu Tatina
Format: Article
Language:English
Published: Elsevier 2022-01-01
Series:Results in Chemistry
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S2211715622000662
Description
Summary:A simple and environment-friendly citric acid-mediated synthesis of glycosides has been reported using Ferrier-rearrangement. Using this protocol, synthesis of several glycosides including pseudo disaccharides was prepared. Citric acid was successfully employed for the synthesis of glycosides from D-glucal, L-rhamnal, D-xylal and D-galactal with various alcohols to give a broad range of glycosides in up to 80% yields with α-isomer as major product under mild reaction conditions.
ISSN:2211-7156