Issue 45, 2020

Transition metal catalyzed glycosylation reactions – an overview

Abstract

Carbohydrates are a large class of natural products that play key roles in a number of biological processes such as in cellular communication or disease progression. Carbohydrates are also used as vaccines and pharmaceuticals. Their synthesis through glycosylation reactions is challenging, and often stoichiometric amounts of promoters are required. Transition metal catalyzed glycosylation reactions are far less common, but can have advantages with respect to reaction conditions and selectivity. The review intends to approach the topic from the catalysis and carbohydrate perspective to encourage researchers from both the fields to perform research in the area. The article covers the basics in glycosylation and catalysis chemistry. The catalysts for the reaction can be roughly divided into two groups. In one group, the catalysts serve as Lewis acids. In the other group, the catalysts play a higher sophisticated role, are involved in all elementary steps of the mechanism and remain coordinated to the substrate throughout the whole catalytic cycle. Based on selected examples, the main trends in transition metal catalyzed glycosylation reactions are explained. Lewis acid catalysts tend to require a somewhat higher catalyst load compared to other organometallic catalysts. The reaction conditions such as the temperature and time depend in many cases on the leaving group employed. An outlook is also presented. The article is not meant to be comprehensive; it outlines the most common transition metal catalyzed processes with the intention to bring the catalysis and carbohydrate communities together and to inspire research activities in both areas.

Graphical abstract: Transition metal catalyzed glycosylation reactions – an overview

Article information

Article type
Review Article
Submitted
27 अगस्त 2020
Accepted
12 अक्तूबर 2020
First published
12 अक्तूबर 2020

Org. Biomol. Chem., 2020,18, 9160-9180

Transition metal catalyzed glycosylation reactions – an overview

E. B. Bauer, Org. Biomol. Chem., 2020, 18, 9160 DOI: 10.1039/D0OB01782E

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