title: Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-D-Mannopyranosyl Sulfones.
abstract: An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and α-D-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access α-D-mannopyranosyl sulfones in good yields with high regioselectivity.
authors.affiliation: D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India.
authors.forename: Sravanthi
authors.initials: S
authors.lastname: Chittela
authors.affiliation: D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India.
authors.forename: Thurpu Raghavender
authors.initials: TR
authors.lastname: Reddy
authors.affiliation: D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India.
authors.forename: Palakodety
authors.initials: P
authors.lastname: Radha Krishna
authors.affiliation: D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India.
authors.forename: Sudhir
authors.initials: S
authors.lastname: Kashyap
mesh_terms: D002384:Catalysis; D006031:Glycosylation; D008358:Mannose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D054330:Thiosugars / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D054330:Thiosugars; D012428:Ruthenium; D008358:Mannose