Issue 17, 2020

Recent advances in β-l-rhamnosylation

Abstract

L-Rhamnose forms the key components of important antigenic oligo- and polysaccharides of a variety of pathogens. Obtaining 1,2-cis stereoselectivity in the glycosylation of L-rhamnoside is quite challenging due to the unavailability of neighboring group participation and disfavoring of the anomeric effect and stereoelectronic effect of the substituents on the C-2 axial position. Nevertheless, various methodologies have been developed exploiting diverse pathways for obtaining β-stereoselectivity in the glycosylation of L-rhamnose. This review describes the recent advances in β-L-rhamnosylation and its applications in the total synthesis of β-L-rhamnose-containing biologically important oligosaccharides.

Graphical abstract: Recent advances in β-l-rhamnosylation

Article information

Article type
Review Article
Submitted
10 Feb 2020
Accepted
30 Mar 2020
First published
30 Mar 2020

Org. Biomol. Chem., 2020,18, 3216-3228

Recent advances in β-L-rhamnosylation

D. Rai and S. S. Kulkarni, Org. Biomol. Chem., 2020, 18, 3216 DOI: 10.1039/D0OB00297F

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