title: Solvent-free bismuth oxycarbonate-mediated mechanochemical glycosylation: A simple greener alternative to access O-/S-glycosides efficiently.
abstract: Preparation of a variety of per-O-acylated O- and S-glycosides of a set of commonly encountered mono- and disaccharides has been achieved effectively by solvent-free grinding of the corresponding acetylated/benzoylated glycosyl bromide and the desired acceptor alcohol/thiol in the presence of bismuth carbonate in a planetary ball mill. The method is simple, requires short reaction time periods and is practical allowing it to be performed at a milligram-to multi-gram scale as required. In the cases where the product is crystalline, it was often obtained in practically pure form by crystallization (and without the need for chromatographic isolation).
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, S.A.S. Nagar, Punjab, 160062, India.
authors.forename: Kashmir Prasad
authors.initials: KP
authors.lastname: Sethi
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, S.A.S. Nagar, Punjab, 160062, India. Electronic address: rkartha@niper.ac.in.
authors.forename: K P Ravindranathan
authors.initials: KP
authors.lastname: Kartha
mesh_terms: D001729:Bismuth / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D003460:Crystallization; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D055772:Green Chemistry Technology; D015394:Molecular Structure
chemical_list: D002254:Carbonates; D006027:Glycosides; C034054:bismuth carbonate; D001729:Bismuth
keywords: Ball milling; Bismuth oxycarbonate catalyst; Mechanochemical glycosylation; Solvent-free glycosylation