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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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
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spelling todo:paper_09473440_v_n9_p1983_Cirelli2023-10-03T15:49:22Z Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides Cirelli, A.F. Moradei, O. Thiem, J. Carbohydrates Epoxidations Glycosides Thromboxane model compounds 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. Fil:Moradei, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09473440_v_n9_p1983_Cirelli
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Carbohydrates
Epoxidations
Glycosides
Thromboxane model compounds
spellingShingle Carbohydrates
Epoxidations
Glycosides
Thromboxane model compounds
Cirelli, A.F.
Moradei, O.
Thiem, J.
Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides
topic_facet Carbohydrates
Epoxidations
Glycosides
Thromboxane model compounds
description 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.
format JOUR
author Cirelli, A.F.
Moradei, O.
Thiem, J.
author_facet Cirelli, A.F.
Moradei, O.
Thiem, J.
author_sort Cirelli, A.F.
title Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides
title_short Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides
title_full Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides
title_fullStr Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides
title_full_unstemmed Synthesis of thromboxane A2 models from glucose, II. Epoxidation studies of hex-2-enopyranosides
title_sort synthesis of thromboxane a2 models from glucose, ii. epoxidation studies of hex-2-enopyranosides
url http://hdl.handle.net/20.500.12110/paper_09473440_v_n9_p1983_Cirelli
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AT moradeio synthesisofthromboxanea2modelsfromglucoseiiepoxidationstudiesofhex2enopyranosides
AT thiemj synthesisofthromboxanea2modelsfromglucoseiiepoxidationstudiesofhex2enopyranosides
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