Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides

The synthesis of halohydrin 7, a potential precursor of the heterocyclic moiety of thromboxane A2 (TXA2) is described. Claisen-Meerwein-Eschenmoser rearrangement of hex-3-enopyranosides 4 and 8 yields the branched olefin sugars 5 and 9. Epoxidation studies with perbenzimidic acid (Payne's metho...

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Detalles Bibliográficos
Autores principales: Cirelli, A.F., Moradei, O., Thiem, J.
Formato: JOUR
Materias:
Carbohydrates
Epoxidations
Glycosides
Thromboxane model compounds
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_09473440_v_n9_p1983_Cirelli
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario:The synthesis of halohydrin 7, a potential precursor of the heterocyclic moiety of thromboxane A2 (TXA2) is described. Claisen-Meerwein-Eschenmoser rearrangement of hex-3-enopyranosides 4 and 8 yields the branched olefin sugars 5 and 9. Epoxidation studies with perbenzimidic acid (Payne's method) and m-chloroperbenzoic acid (Anderson's method) were performed. Under treatment of the 2,3-anhydrosugar 6 with LiBr, the epimeric halohydrins 7 and 10 were obtained in a ratio of 3:2. © VCH Verlagsgesellschaft mbH, 1997.

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