title: Gold mediated glycosylations: selective activation of propargyl 1,2-orthoesters in the presence of aglycones containing a propargyl moiety.
abstract: Selective activation of propargyl 1,2-orthoesters in the presence of propargyl glycosides and propargyl ethers was studied; a catalytic amount of AuBr3 activated the propargyloxy group of the 1,2-orthoester thereby giving access to disaccharides with the propargyl group at the reducing end; furthermore, propargyl ethers were unaffected under the reaction conditions.
authors.affiliation: Division of Organic Chemistry, Combi Chem-Bio Resource Center, National Chemical Laboratory, Pune, 411 008, India.
authors.forename: Gopalsamy
authors.initials: G
authors.lastname: Sureshkumar
authors.forename: Srinivas
authors.initials: S
authors.lastname: Hotha
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D004187:Disaccharides; D004952:Esters; D004987:Ethers; D006027:Glycosides; D020005:Propanols; D006046:Gold; C028255:propargyl alcohol