title: Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors.
abstract: Propargyl 1,2-O-orthoesters are exploited for the synthesis of 1,2-trans O-glycosides of protected amino acids. N-Fmoc- and N-Cbz protected serine/threonine - benzyl/methyl esters reacted well with glucosyl-, galactosyl-, mannosyl- and lactosyl- derived propargyl 1,2-orthoesters affording respective 1,2-trans glycosides in good yields under AuBr(3)/4 Å MS Powder/CH(2)Cl(2)/rt. t-Boc serine derivative gave serine 1,2-orthoester and glycosyl carbamate. Optimized conditions enabled preparation of new glycosyl carbamates from N-Boc protected amines in a single step using gold catalysts and propargyl 1,2-orthoesters in excellent yields.
authors.affiliation: Division of Organic Chemistry, Combi Chem-Bio Resource Center, National Chemical Laboratory, Pune, 411008, India.
authors.forename: Ashif Y
authors.initials: AY
authors.lastname: Shaikh
authors.forename: Gopalsamy
authors.initials: G
authors.lastname: Sureshkumar
authors.forename: Debasish
authors.initials: D
authors.lastname: Pati
authors.forename: Sayam
authors.initials: S
authors.lastname: Sen Gupta
authors.forename: Srinivas
authors.initials: S
authors.lastname: Hotha
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000596:Amino Acids; D002219:Carbamates; D004952:Esters; D006027:Glycosides