1330004-38-0Relevant academic research and scientific papers
Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates
D'Angelo, Kyan A.,Taylor, Mark S.
, p. 11058 - 11066 (2016/09/12)
In the presence of a diarylborinic acid catalyst, glycosyl methanesulfonates engage in regio- and stereoselective couplings with partially protected pyranoside and furanoside acceptors. The methanesulfonate donors are prepared in situ from glycosyl hemiacetals, and are coupled under mild, operationally simple conditions (amine base, organoboron catalyst, room temperature). The borinic acid catalyst not only influences site-selectivity via activation of 1,2- or 1,3-diol motifs, but also has a pronounced effect on the stereochemical outcome: 1,2-trans-linked disaccharides are obtained selectively in the absence of neighboring group participation. Reaction progress kinetic analysis was used to obtain insight into the mechanism of glycosylation, both in the presence of catalyst and in its absence, while rates of interconversion of methanesulfonate anomers were determined by NMR exchange spectroscopy (EXSY). Together, the results suggest that although the uncatalyzed and catalyzed reactions give rise to opposite stereochemical outcomes, both proceed by associative mechanisms.
Regioselective activation of glycosyl acceptors by a diarylborinic acid-derived catalyst
Gouliaras, Christina,Lee, Doris,Chan, Lina,Taylor, Mark S.
, p. 13926 - 13929 (2011/10/31)
A derivative of diphenylborinic acid promotes catalytic, regioselective Koenigs-Knorr glycosylations of carbohydrate derivatives bearing multiple secondary hydroxyl groups. Robust levels of selectivity for the equatorial OH group of cis-1,2-diol motifs ar
