Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime
We report the synthesis of 5-[5'-(1',2':3',4'-di-O-isopropylidene-β-L- arabinopyranosyl)]tetrazole, from 1,2:3,4-di-O-isopropylidene-α-D-galacto- 1,6-hexodialdo-1,5-pyranose oxime via 1,2:3,4-di-O-isopropylidene-α-D- galacturononitrile as intermediate by 1,3-dipolar cycloadd...
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todo:paper_0022152X_v36_n1_p177_MartinsAlho2023-10-03T14:27:44Z Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime Martins Alho, M.A. D'Accorso, N.B. 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl]tetrazole 5 methyl 2 [5' (1',2':3',4' di o isoproylidene beta levo arabinosyl] 1,3,4 oxadiazole 5 phenyl 2 [5' (1',2':3',4' di o isoproylidene beta levo arabinosyl] 1,3,4 oxadiazole heterocyclic compound oxadiazole derivative tetrazole derivative unclassified drug article carbon nuclear magnetic resonance chemical reaction chemical structure organic chemistry proton nuclear magnetic resonance synthesis We report the synthesis of 5-[5'-(1',2':3',4'-di-O-isopropylidene-β-L- arabinopyranosyl)]tetrazole, from 1,2:3,4-di-O-isopropylidene-α-D-galacto- 1,6-hexodialdo-1,5-pyranose oxime via 1,2:3,4-di-O-isopropylidene-α-D- galacturononitrile as intermediate by 1,3-dipolar cycloaddition. We also report the synthesis of 5-methyl- and 5-phenyl-2-[5'-(1',2':3',4',-di-O- isopropylidene-β-L-arabinopyranosyl)]-1,3,4-oxadiazole from the tetrazole derivative. The physical and spectroscopic characterizations of the heterocyclic derivatives as well as the intermediate nitrile and the principal byproduct are described and we discuss its possible formation pathway. We present the preferential conformation in solution using computational calculation and spectroscopic data. Fil:Martins Alho, M.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:D'Accorso, N.B. 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_0022152X_v36_n1_p177_MartinsAlho |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl]tetrazole 5 methyl 2 [5' (1',2':3',4' di o isoproylidene beta levo arabinosyl] 1,3,4 oxadiazole 5 phenyl 2 [5' (1',2':3',4' di o isoproylidene beta levo arabinosyl] 1,3,4 oxadiazole heterocyclic compound oxadiazole derivative tetrazole derivative unclassified drug article carbon nuclear magnetic resonance chemical reaction chemical structure organic chemistry proton nuclear magnetic resonance synthesis |
| spellingShingle |
5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl]tetrazole 5 methyl 2 [5' (1',2':3',4' di o isoproylidene beta levo arabinosyl] 1,3,4 oxadiazole 5 phenyl 2 [5' (1',2':3',4' di o isoproylidene beta levo arabinosyl] 1,3,4 oxadiazole heterocyclic compound oxadiazole derivative tetrazole derivative unclassified drug article carbon nuclear magnetic resonance chemical reaction chemical structure organic chemistry proton nuclear magnetic resonance synthesis Martins Alho, M.A. D'Accorso, N.B. Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime |
| topic_facet |
5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl]tetrazole 5 methyl 2 [5' (1',2':3',4' di o isoproylidene beta levo arabinosyl] 1,3,4 oxadiazole 5 phenyl 2 [5' (1',2':3',4' di o isoproylidene beta levo arabinosyl] 1,3,4 oxadiazole heterocyclic compound oxadiazole derivative tetrazole derivative unclassified drug article carbon nuclear magnetic resonance chemical reaction chemical structure organic chemistry proton nuclear magnetic resonance synthesis |
| description |
We report the synthesis of 5-[5'-(1',2':3',4'-di-O-isopropylidene-β-L- arabinopyranosyl)]tetrazole, from 1,2:3,4-di-O-isopropylidene-α-D-galacto- 1,6-hexodialdo-1,5-pyranose oxime via 1,2:3,4-di-O-isopropylidene-α-D- galacturononitrile as intermediate by 1,3-dipolar cycloaddition. We also report the synthesis of 5-methyl- and 5-phenyl-2-[5'-(1',2':3',4',-di-O- isopropylidene-β-L-arabinopyranosyl)]-1,3,4-oxadiazole from the tetrazole derivative. The physical and spectroscopic characterizations of the heterocyclic derivatives as well as the intermediate nitrile and the principal byproduct are described and we discuss its possible formation pathway. We present the preferential conformation in solution using computational calculation and spectroscopic data. |
| format |
JOUR |
| author |
Martins Alho, M.A. D'Accorso, N.B. |
| author_facet |
Martins Alho, M.A. D'Accorso, N.B. |
| author_sort |
Martins Alho, M.A. |
| title |
Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime |
| title_short |
Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime |
| title_full |
Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime |
| title_fullStr |
Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime |
| title_full_unstemmed |
Synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-O-isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose oxime |
| title_sort |
synthesis and characterization of some heterocyclic derivatives from 1,2:3,4-di-o-isopropylidene-α-d-galacto-1,6-hexadialdo-1,5-pyranose oxime |
| url |
http://hdl.handle.net/20.500.12110/paper_0022152X_v36_n1_p177_MartinsAlho |
| work_keys_str_mv |
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