The glycosidation of phenols with 2,3,4,6-tetra-O-acetyl-α-D- glucopyranosyl fluoride in the presence of BF3OEt2 to give, predominantly, α-anomers has been studied. In the presence of an amine base, 1,1,3,3-tetramethylguanidine, however, enhanced β-selectivity was achieved. The former reaction provides a novel and useful synthesis of aryl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside whilst the latter is effective for the glycosidation of relatively hindered phenols.
|Number of pages||4|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - 1990|
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