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
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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
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Palabras clave: | Carbohydrates; Epoxidations; Glycosides; Thromboxane model compounds |
Año: | 1997
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Número: | 9
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Página de inicio: | 1983
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Página de fin: | 1987
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DOI: |
http://dx.doi.org/10.1002/jlac.199719970926 |
Título revista: | Liebigs Annales
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ISSN: | 09473440
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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