title: Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite.
abstract: A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-D-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
authors.forename: Cheerladinne
authors.initials: C
authors.lastname: Venkateswarlu
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
authors.forename: Vibha
authors.initials: V
authors.lastname: Gautam
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India. Electronic address: scn@orgchem.iisc.ernet.in.
authors.forename: Srinivasan
authors.initials: S
authors.lastname: Chandrasekaran
mesh_terms: D002384:Catalysis; D002475:Cellobiose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis; D009942:Organometallic Compounds / Q000138:chemical synthesis*; D013441:Sulfinic Acids / Q000737:chemistry*; D014468:Umbelliferones / Q000138:chemical synthesis*
chemical_list: C453491:4-methyl-7-thioumbelliferylcellobioside; D006027:Glycosides; D009942:Organometallic Compounds; D013441:Sulfinic Acids; D014468:Umbelliferones; D002475:Cellobiose; C011111:formaldehydesulfoxylate
keywords: Diaryl dichalcogenide; Phenyl selenoglycoside; Reductive cleavage; Rongalite; Thioglycoside