PMID: 11916390Mar 28, 2002Paper

Unexpected role of O-2 "protecting" groups of glycosyl donors in mediating regioselective glycosidation

Journal of the American Chemical Society
Bert Fraser-ReidClara Uriel

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.

References

Sep 16, 2000·Organic Letters·G AnilkumarB Fraser-Reid

❮ Previous
Next ❯

Citations

Jan 29, 2009·Angewandte Chemie·Xiangming Zhu, Richard R Schmidt
Nov 11, 2016·Beilstein Journal of Organic Chemistry·Madhuri Vangala, Ganesh P Shinde
Sep 15, 2011·Chemistry : a European Journal·Chin-Sheng ChaoKwok-kong Tony Mong
Nov 8, 2008·The Journal of Organic Chemistry·Bert Fraser-ReidChangalvala V S Ramamurty
Dec 7, 2018·Chemical Reviews·Victoria Dimakos, Mark S Taylor
Oct 12, 2002·The Journal of Organic Chemistry·Andréas Meijer, Ulf Ellervik

❮ Previous
Next ❯

Related Concepts

Related Feeds

Cardiac Glycosides

Cardiac glycosides are a diverse family of naturally derived compounds that bind to and inhibit na+/k+-atpase. Discover the latest research on cardiac glycosides heres.