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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.

SUBMITTER: Hesek D

PROVIDER: S-EPMC2846112 | biostudies-literature | 2008 Sep

REPOSITORIES: biostudies-literature

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Facile preparation of a highly functionalized tetrahydropyran by catalytic hydrogenation of an oxazoline.

Hesek Dusan D Lee Mijoon M Yamaguchi Takao T Noll Bruce C BC Mobashery Shahriar S

The Journal of organic chemistry 20080809 18

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. ...[more]

PMID: 18690743

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