Issue 45, 2022

Silane promoted glycosylation and its applications for synthesis of sugar compounds and active pharmaceutical ingredients (APIs)

Abstract

The structural diversity of carbohydrates through glycosylation reactions is the holy grail of carbohydrate chemistry. One or more carbohydrates covalently bonded to another molecule at selective sites by glycosylation/glycoconjugation are often required for better pharmacological activity and their synthesis is apparently more consistent. Selective conjugation of carbohydrates at the –OH group remains a challenge because of the similar reactivity of equivalent polyhydroxyl groups. Eventually a small variety of reagents have been demonstrated to promote site selective glycosylation reactions. Silanes have long provided a leverage in glycosylation reactions since they are easy to install and remove/modify in various synthetic procedures. Regardless of the fact that silanes have proven to be efficient promoters for facile glycoconjugation reactions, a thorough investigation has not been done on this subject. This review discusses the recent application and synthetic usefulness of versatile silanes like trimethylsilyl trifluoromethanesulfonate (TMSOTf), tert-butyldimethylsilyltrifluoromethanesulphonate (TBSOTf), N-(trimethylsilyl)bis(trifluoromethanesulfonyl)imide (TMSNTf2), potassium bis(trimethylsilyl)amide (KHMDS), trimethylsilyl perchlorate (TMSClO4), etc. in various site selective glycosylation reactions and also effective methods for the preparation of sugar compounds and active pharmaceutical ingredients (APIs).

Graphical abstract: Silane promoted glycosylation and its applications for synthesis of sugar compounds and active pharmaceutical ingredients (APIs)

Article information

Article type
Perspective
Submitted
24 محرم 1444
Accepted
21 ربيع الأول 1444
First published
23 ربيع الأول 1444

New J. Chem., 2022,46, 21519-21535

Silane promoted glycosylation and its applications for synthesis of sugar compounds and active pharmaceutical ingredients (APIs)

S. S. Kar, N. P. Nanda, V. Ravichandiran and S. P. Swain, New J. Chem., 2022, 46, 21519 DOI: 10.1039/D2NJ04192H

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