Orthogonal One-Pot Synthesis of Oligosaccharides Based on Glycosyl ortho-Alkynylbenzoates.

Org Lett

State Key Laboratory of Phytochemistry and Plant Resources in West China , Kunming Institute of Botany, University of Chinese Academy of Sciences, Chinese Academy of Sciences , Kunming 650201 , China.

Published: April 2019

One of the most popular one-pot glycosylation strategies is orthogonal one-pot synthesis, which was mainly based on thioglycosides. Despite its successful application, shortcomings of thioglycosides including aglycon transfers, interference of departing species and unpleasant odor restrict its application scope. Herein, we report a new and efficient orthogonal one-pot synthesis of oligosaccahrides based on glycosyl ortho-alkynylbenzoate, which solves the issues of thioglycoside-based orthogonal one-pot synthesis. Over a dozen of oligosaccharides have been efficiently synthesized by this method.

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http://dx.doi.org/10.1021/acs.orglett.9b00617DOI Listing

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