AI Article Synopsis
- - The study addresses issues with the inefficient preparation of a specific donor compound used in glycosylation, which has previously shown excellent β-selectivity.
- - The authors present an enhanced method for creating the donor, focusing on refining the process of forming a 3,6-bridge on a specific type of glucose.
- - They discovered that the bridged glucose prefers a furanose form, but solved synthesis challenges through thermal glycosylation, which could increase the donor's availability for wider use.
Article Abstract
Despite the reported complete β-selectivity in glycosylation with 2,4-di-O-benzyl-3,6-O-(o-xylylene)glucopyranosyl fluoride, its preparation has been inefficient. This paper describes an improved route for the donor, including the formation of the 3,6-bridge on 1,2,4-orthoacetylglucose, the preparation of which was also refined, along with a discovered feature that the 3,6-bridged glucose prefers the furanose form. Although this feature made the synthesis of the desired glucopyranosyl donor difficult, application of thermal glycosylation solved the problem. With a modifiable intermediate, the improved availability of the donor would expand the applications.
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| http://dx.doi.org/10.1021/jo401395h | DOI Listing |
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