title: Facile preparation of a highly functionalized tetrahydropyran by catalytic hydrogenation of an oxazoline.
abstract: 2-Amino-1,5-anhydro-2-deoxy-D-glucitol, a highly functionalized tetrahydropyran, is a versatile building unit in many natural products. A facile route to this type of synthetic building unit from the corresponding 2-aminopyranoses, as exemplified by an application to D-glucosamine, is outlined. A simple catalytic hydrogenation at C-1 of an oxazoline constructed from the corresponding 2-aminopyranose results in the desired product.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
authors.forename: Dusan
authors.initials: D
authors.lastname: Hesek
authors.forename: Mijoon
authors.initials: M
authors.lastname: Lee
authors.forename: Takao
authors.initials: T
authors.lastname: Yamaguchi
authors.forename: Bruce C
authors.initials: BC
authors.lastname: Noll
authors.forename: Shahriar
authors.initials: S
authors.lastname: Mobashery
mesh_terms: D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002236:Carbohydrate Conformation; D002384:Catalysis; D018360:Crystallography, X-Ray; D006865:Hydrogenation; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008958:Models, Molecular; D010080:Oxazoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012015:Reference Standards
chemical_list: D010080:Oxazoles; D011714:Pyrans; D010165:Palladium; C086406:1-deoxy-N-acetylglucosamine; D000117:Acetylglucosamine