Issue 44, 2020

Chemoselective activation of ethyl vs. phenyl thioglycosides: one-pot synthesis of oligosaccharides

Abstract

Ethyl and phenyl thioglycosides are the two most common types of thioglycoside donors in carbohydrate chemistry. However, the chemoselective activation of ethyl vs. phenyl thioglycosides is very rare in the literature. In this work, ethyl thioglycosides could be readily activated with an N-trifluoromethylthiosaccharin/TMSOTf system in the presence of phenyl thioglycosides carrying the same or even more armed protecting group pattern. Both armed and disarmed thioglycosides exhibited high chemoselectivity towards the promoter system. Chemoselective glycosylation was subsequently applied to one-pot synthesis, thus providing an efficient means to oligosaccharides.

Graphical abstract: Chemoselective activation of ethyl vs. phenyl thioglycosides: one-pot synthesis of oligosaccharides

Supplementary files

Article information

Article type
Communication
Submitted
04 8 2020
Accepted
24 8 2020
First published
24 8 2020

Org. Biomol. Chem., 2020,18, 9029-9034

Chemoselective activation of ethyl vs. phenyl thioglycosides: one-pot synthesis of oligosaccharides

C. Mc Carthy and X. Zhu, Org. Biomol. Chem., 2020, 18, 9029 DOI: 10.1039/D0OB01606C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements