Facile preparation of a highly functionalized tetrahydropyran by catalytic hydrogenation of an oxazoline.
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.
Hesek
Dusan
D
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Lee
Mijoon
M
Yamaguchi
Takao
T
Noll
Bruce C
BC
Mobashery
Shahriar
S
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
D010080:Oxazoles; D011714:Pyrans; D010165:Palladium; C086406:1-deoxy-N-acetylglucosamine; D000117:Acetylglucosamine