title: Facile synthesis of aminooxy glycosides by gold(III)-catalyzed glycosidation.
abstract: The O-glycosidation of hydroxysuccinimides and hydroxyphthalimides with a variety of aldose derived propargyl 1,2-orthoesters under the gold(III)-catalyzed glycosidation conditions is reported. A wide range of hydroxysuccinimidyl and hydroxyphthalimidyl glycosides were synthesized from corresponding glycosyl orthoesters including glucosyl, mannosyl, galactosyl, ribofuranosyl, arabinofuranosyl, lyxofuranosyl and xylofuranosyl using gold catalysis repertoire. The protocol is identified to be compatible for the synthesis of aminooxy glycosides of higher oligosaccharides as well.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education & Research, Pune 411 008, India.
authors.forename: Shivaji A
authors.initials: SA
authors.lastname: Thadke
authors.affiliation: Department of Chemistry, Indian Institute of Science Education & Research, Pune 411 008, India.
authors.forename: Mahesh
authors.initials: M
authors.lastname: Neralkar
authors.affiliation: Department of Chemistry, Indian Institute of Science Education & Research, Pune 411 008, India. Electronic address: s.hotha@iiserpune.ac.in.
authors.forename: Srinivas
authors.initials: S
authors.lastname: Hotha
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D006046:Gold
keywords: Chemical synthesis; Glycosides; Gold catalysis; Oligosaccharides