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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides
Autor:Cirelli, A.F.; Moradei, O.; Thiem, J.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pab. II, (1428), Buenos Aires, Argentina
Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany
Palabras clave:Carbohydrates; Epoxidations; Glycosides; Thromboxane model compounds
Año:1997
Número:9
Página de inicio:1983
Página de fin:1987
DOI: http://dx.doi.org/10.1002/jlac.199719970926
Título revista:Liebigs Annales
ISSN:09473440
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09473440_v_n9_p1983_Cirelli

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Citas:

---------- APA ----------
Cirelli, A.F., Moradei, O. & Thiem, J. (1997) . Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides. Liebigs Annales(9), 1983-1987.
http://dx.doi.org/10.1002/jlac.199719970926
---------- CHICAGO ----------
Cirelli, A.F., Moradei, O., Thiem, J. "Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides" . Liebigs Annales, no. 9 (1997) : 1983-1987.
http://dx.doi.org/10.1002/jlac.199719970926
---------- MLA ----------
Cirelli, A.F., Moradei, O., Thiem, J. "Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides" . Liebigs Annales, no. 9, 1997, pp. 1983-1987.
http://dx.doi.org/10.1002/jlac.199719970926
---------- VANCOUVER ----------
Cirelli, A.F., Moradei, O., Thiem, J. Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides. 1997(9):1983-1987.
http://dx.doi.org/10.1002/jlac.199719970926