Reactivity, Selectivity, and Synthesis of 4-C-Silylated Glycosyl Donors and 4-Deoxy Analogues
Research output: Contribution to journal › Journal article › Research › peer-review
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.
Original language | English |
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Journal | Angewandte Chemie - International Edition |
Volume | 60 |
Issue number | 5 |
Pages (from-to) | 2689-2693 |
Number of pages | 5 |
ISSN | 1433-7851 |
DOIs | |
Publication status | Published - 2021 |
Bibliographical note
Publisher Copyright:
© 2020 Wiley-VCH GmbH
- glycosylation, levoglucosenone, selectivity, silylation, synthesis
Research areas
ID: 270204454