Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 1079-1082 |
| Number of pages | 4 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 1990 |
ASJC Scopus subject areas
- Chemistry(all)
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Yamaguchi, M., Horiguchi, A., Fukuda, A., & Minami, T. (1990). Novel synthesis of aryl 2,3,4,6-tetra-O-acetyl-D-glucopyranosides. Journal of the Chemical Society, Perkin Transactions 1, (4), 1079-1082. https://doi.org/10.1039/p19900001079