62396-57-0Relevant academic research and scientific papers
Synthesis, NMR, and conformational studies of fucoidan fragments. III. Effect of benzoyl group at O-3 on stereoselectivity of glycosylation by 3-0- and 3,4-DI-0-benzoylated 2-0-benzylfucosyl bromides
Gerbst, Alexey G.,Ustuzhanina, Nadezhda E.,Grachev, Alexey A.,Khatuntseva, Elena A.,Tsvetkov, Dmitry E.,Whitfield, Dennis M.,Berces, Attila,Nifantiev, Nikolay E.
, p. 821 - 831 (2001)
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.
