6814-93-3Relevant academic research and scientific papers
Boron Effect on Sugar-Based Organogelators
Ludwig, Andreas D.,Saint-Jalmes, Arnaud,Mériadec, Cristelle,Artzner, Franck,Tasseau, Olivier,Berrée, Fabienne,Lemiègre, Lo?c
, p. 13927 - 13934 (2020)
The reaction of several alkylglucosides with phenyl boronic acid permitted easy access to a series of alkylglucoside phenyl boronate derivatives. This type of compound has structures similar to those of known benzylidene glucoside organogelators except fo
Regioselective glycosylation of unprotected phenyl 1-thioglycopyranosides with phenylboronic acid as a transient masking group
Fenger, Thomas Hauch,Madsen, Robert
, p. 5923 - 5933 (2013/09/23)
A useful protocol is described for the regioselective glycosylation of the secondary alcohols in unprotected glycosyl acceptors. Phenyl 1-thioglycopyranosides derived from D-glucose, D-galactose, D-glucosamine, L-rhamnose, and L-fucose were treated with phenylboronic acid to install a temporary boronic ester, and then submitted to a Koenigs-Knorr glycosylation with perbenzoylated glucopyranosyl or galactopyranosyl bromides. Good yields for coupling to the 3-position in glucosides and galactosides were achieved, but lower yields were obtained with the other acceptors. With phenyl 1-thio-β-D-glucopyranoside, the coupling could also be achieved with a superarmed thiogalactoside donor. The product from a glucose-glucose coupling could be subjected to a second regioselective glycosylation at the 6-position. In the galactose series, a β(1→3)-linked galactotriose could be prepared in good yield by two consecutive glycosylations in one pot, where a free 2-hydroxy group ensures neighboring group participation in the second coupling. Unprotected phenyl 1-thioglycopyranosides are protected in situ with phenylboronic acid and regioselectively glycosylated under Koenigs-Knorr conditions. The product disaccharides can be used directly as donors or acceptors for an additional glycosylation reaction. Copyright
