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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Autores principales:	Martins Alho, Miriam Amelia, D'Accorso, Norma Beatriz
Publicado:	1999
Materias:	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
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v36_n1_p177_MartinsAlho http://hdl.handle.net/20.500.12110/paper_0022152X_v36_n1_p177_MartinsAlho
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_0022152X_v36_n1_p177_MartinsAlho
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spelling	paper:paper_0022152X_v36_n1_p177_MartinsAlho2023-06-08T14:46:46Z 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, Miriam Amelia D'Accorso, Norma Beatriz 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. 1999 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v36_n1_p177_MartinsAlho http://hdl.handle.net/20.500.12110/paper_0022152X_v36_n1_p177_MartinsAlho
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	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, Miriam Amelia D'Accorso, Norma Beatriz 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.
author	Martins Alho, Miriam Amelia D'Accorso, Norma Beatriz
author_facet	Martins Alho, Miriam Amelia D'Accorso, Norma Beatriz
author_sort	Martins Alho, Miriam Amelia
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
publishDate	1999
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v36_n1_p177_MartinsAlho http://hdl.handle.net/20.500.12110/paper_0022152X_v36_n1_p177_MartinsAlho
work_keys_str_mv	AT martinsalhomiriamamelia synthesisandcharacterizationofsomeheterocyclicderivativesfrom1234dioisopropylideneadgalacto16hexadialdo15pyranoseoxime AT daccorsonormabeatriz synthesisandcharacterizationofsomeheterocyclicderivativesfrom1234dioisopropylideneadgalacto16hexadialdo15pyranoseoxime
_version_	1768544352093601792

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

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