Bimodal Glycosyl Donors as an Emerging Approach Towards a General Glycosylation Strategy.

Autor: Warnes ME; Department of Chemistry, University of York, York, YO10 5DD, UK., Fascione MA; Department of Chemistry, University of York, York, YO10 5DD, UK.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 May 23; Vol. 30 (29), pp. e202400399. Date of Electronic Publication: 2024 Apr 17.
DOI: 10.1002/chem.202400399
Abstrakt: Organic synthesis provides an accessible route to preparative scale biological glycans, although schemes to access these complex structures are often complicated by preparation of multiple monosaccharide building blocks. Bimodal glycosyl donors capable of forming both α- and β-anomers selectively, are an emerging tactic to reduce the required number of individual synthetic components in glycan construction. This review discusses examples of bimodal donors in the literature, and how they achieve their stereocontrol for both anomers. Notable examples include a bespoke O-2 benzyl protecting group, a strained glycal for reaction using organometallic catalysis, and a simple perbenzylated donor optimised for stereoselective glycosylation through extensive reaction tuning.
(© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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