Journal of Carbohydrate Chemistry p. 821 - 831 (2001)
Update date:2022-09-26
Topics:
Gerbst, Alexey G.
Ustuzhanina, Nadezhda E.
Grachev, Alexey A.
Khatuntseva, Elena A.
Tsvetkov, Dmitry E.
Whitfield, Dennis M.
Berces, Attila
Nifantiev, Nikolay E.
The effect of a benzoyl group at O-3 on stereoselectivity of glycosylation by 3-0-and 3,4-di-0-benzoylated 2-0-benzyl-L-fucopyranosyl bromides was studied by direct chemical experiments and computational chemistry. The influence of a benzoyl group at O-3 of the fucosyl donors was shown to have a larger effect on the efficiency of α-fucosylation than a benzoyl group at O-4. It is hypothesized that this is a result of the ability of a benzoyl group at O-3 to participate in glycosyl cation stabilization.
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