Reactivity, Selectivity, and Synthesis of 4-C-Silylated Glycosyl Donors and 4-Deoxy Analogues
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
A method for introducing dimethylphenylsilyl at the 4-position in carbohydrates has been developed. Two C-silylated glycosyl donors were prepared via levoglucosenone, starting from cellulose. The glycosylation properties were studied using three glucoside acceptors, a 3-OH, 4-OH, and 6-OH. Compared with the 4-deoxy variant, it was found that the anomeric selectivity was influenced more by the C-2 substituents orientation than the silyl in the 4-position. In general, the reactivity of these donors was higher than the corresponding 4-deoxy-analogue, albeit a competition experiment showed that the introduction of a C−Si increases the relative reactivity by a modest factor of around two.
Originalsprog | Engelsk |
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Tidsskrift | Angewandte Chemie - International Edition |
Vol/bind | 60 |
Udgave nummer | 5 |
Sider (fra-til) | 2689-2693 |
Antal sider | 5 |
ISSN | 1433-7851 |
DOI | |
Status | Udgivet - 2021 |
Bibliografisk note
Funding Information:
The Villum Foundation is acknowledged for a block stipend for MJP.
Publisher Copyright:
© 2020 Wiley-VCH GmbH
ID: 270204454