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Angew Chem Int Ed Engl
; 60(5): 2689-2693, 2021 02 01.
Artigo
em Inglês
| MEDLINE
| ID: mdl-33025650
RESUMO
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.