title: De novo synthesis of 1-deoxythiosugars.
abstract: A short and efficient chemical synthesis of biologically potent and novel 1-deoxythiosugars is accomplished. Introduction of sulfur mediated by benzyltriethylammonium tetrathiomolybdate, as a sulfur transfer reagent through nucleophilic double displacement of tosylate in α,ω-di-O-tosyl aldonolactones in an intramolecular fashion is the key feature. The subsequent reduction of thiosugar lactones with borohydride exchange resin (BER) offers a number of deoxythiosugars in good overall yield.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
authors.forename: Thanikachalam
authors.initials: T
authors.lastname: Gunasundari
authors.forename: Srinivasan
authors.initials: S
authors.lastname: Chandrasekaran
mesh_terms: D001894:Borohydrides / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D007475:Ion Exchange Resins / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D008982:Molybdenum / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry
chemical_list: D001894:Borohydrides; D002241:Carbohydrates; D007475:Ion Exchange Resins; D007783:Lactones; D000644:Quaternary Ammonium Compounds; D013455:Sulfur; D008982:Molybdenum; C020809:tetrathiomolybdate; C556155:benzyltriethylammonium
keywords: 1-Deoxythiosugars; Aldonoditosylate; Borohydride exchange resin; Tetrathiomolybdate; Thiosugar lactone