TY - JOUR
T1 - Novel synthesis of aryl 2,3,4,6-tetra-O-acetyl-D-glucopyranosides
AU - Yamaguchi, Masahiko
AU - Horiguchi, Akira
AU - Fukuda, Akira
AU - Minami, Toru
PY - 1990
Y1 - 1990
N2 - 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.
AB - 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.
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U2 - 10.1039/p19900001079
DO - 10.1039/p19900001079
M3 - Article
AN - SCOPUS:37049072323
SP - 1079
EP - 1082
JO - Journal of the Chemical Society. Perkin Transactions 1
JF - Journal of the Chemical Society. Perkin Transactions 1
SN - 1470-4358
IS - 4
ER -