Unexpected Role of O-2 “Protecting” Groups of Glycosyl Donors in Mediating Regioselective Glycosidation
- 8 March 2002
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (13) , 3198-3199
- https://doi.org/10.1021/ja012383m
Abstract
Glycosidation of several vicinal diols reveals that exquisite regioselectivity can be achieved by using 2-O-benzoyl n-pentenyl glycoside donors and/or their cyclic 1,2-ortho ester counterparts. The regioselective preferences for both are the same, although ratios and yields may differ. In stark contrast, glycosidation of the diols with the corresponding 2-O-benzylated donors gives poor, if any, regioselectivity.Keywords
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