Deprotection of di-O-isopropylidene isocarbonucleosides
Deprotection of 5-glycosyl heterocyclic derivatives of 1,2:3:4-di-O- isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose allowed isocarbonucleoside analogues to be obtained with enhaced solubility in the aqueous medium used for antiviral assays. Looking for a deprotection method of isopropylidene...
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todo:paper_14246376_v2003_n10_p491_MartinezEsperon2023-10-03T16:13:38Z Deprotection of di-O-isopropylidene isocarbonucleosides Martínez Esperón, M.F. Errea, M.I. Martins Alho, M.A. D'Accorso, N.B. Isocarbonucleosides Isopropylidene deprotection Microwaves 1,2:3:4 di o isopropylidene alpha dextro galacto 1,6 hexadialdo 1,5 pyranose derivative 2 amino 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 thiadiazole 2 amino 5 [5' (alpha levo arabinopyranosyl)] 1,3,4 thiadiazole 2 amino 5 [5' (beta levo arabinopyranosyl)] 1,3,4 thiadiazole 2 methyl 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (alpha levo arabinofuranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (alpha levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (beta levo arabinofuranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (beta levo arabinopyranosyl)] 1,3,4 oxadiazole 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)]tetrazole 5 [5' (alpha levo arabinopyranosyl)]tetrazole 5 [5' (beta levo arabinopyranosyl)]tetrazole functional group isocarbonucleoside derivatives isopropylidene n acetyl alpha dextro galacturonopyranosylhydrazide n acetyl beta dextro galacturonopyranosylhydrazide nucleoside derivative unclassified drug antiviral activity article assay carbon nuclear magnetic resonance deprotection reaction heating intermethod comparison microwave radiation proton nuclear magnetic resonance reaction time solubility Deprotection of 5-glycosyl heterocyclic derivatives of 1,2:3:4-di-O- isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose allowed isocarbonucleoside analogues to be obtained with enhaced solubility in the aqueous medium used for antiviral assays. Looking for a deprotection method of isopropylidene groups which would not affect the heterocycle, we performed and compared different deprotection techniques using microwave radiation or thermal heating and found that, in most cases, this goal could be achieved, in short times and good yields, when the reactions were microwave-assisted. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p491_MartinezEsperon |
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Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Isocarbonucleosides Isopropylidene deprotection Microwaves 1,2:3:4 di o isopropylidene alpha dextro galacto 1,6 hexadialdo 1,5 pyranose derivative 2 amino 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 thiadiazole 2 amino 5 [5' (alpha levo arabinopyranosyl)] 1,3,4 thiadiazole 2 amino 5 [5' (beta levo arabinopyranosyl)] 1,3,4 thiadiazole 2 methyl 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (alpha levo arabinofuranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (alpha levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (beta levo arabinofuranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (beta levo arabinopyranosyl)] 1,3,4 oxadiazole 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)]tetrazole 5 [5' (alpha levo arabinopyranosyl)]tetrazole 5 [5' (beta levo arabinopyranosyl)]tetrazole functional group isocarbonucleoside derivatives isopropylidene n acetyl alpha dextro galacturonopyranosylhydrazide n acetyl beta dextro galacturonopyranosylhydrazide nucleoside derivative unclassified drug antiviral activity article assay carbon nuclear magnetic resonance deprotection reaction heating intermethod comparison microwave radiation proton nuclear magnetic resonance reaction time solubility |
| spellingShingle |
Isocarbonucleosides Isopropylidene deprotection Microwaves 1,2:3:4 di o isopropylidene alpha dextro galacto 1,6 hexadialdo 1,5 pyranose derivative 2 amino 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 thiadiazole 2 amino 5 [5' (alpha levo arabinopyranosyl)] 1,3,4 thiadiazole 2 amino 5 [5' (beta levo arabinopyranosyl)] 1,3,4 thiadiazole 2 methyl 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (alpha levo arabinofuranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (alpha levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (beta levo arabinofuranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (beta levo arabinopyranosyl)] 1,3,4 oxadiazole 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)]tetrazole 5 [5' (alpha levo arabinopyranosyl)]tetrazole 5 [5' (beta levo arabinopyranosyl)]tetrazole functional group isocarbonucleoside derivatives isopropylidene n acetyl alpha dextro galacturonopyranosylhydrazide n acetyl beta dextro galacturonopyranosylhydrazide nucleoside derivative unclassified drug antiviral activity article assay carbon nuclear magnetic resonance deprotection reaction heating intermethod comparison microwave radiation proton nuclear magnetic resonance reaction time solubility Martínez Esperón, M.F. Errea, M.I. Martins Alho, M.A. D'Accorso, N.B. Deprotection of di-O-isopropylidene isocarbonucleosides |
| topic_facet |
Isocarbonucleosides Isopropylidene deprotection Microwaves 1,2:3:4 di o isopropylidene alpha dextro galacto 1,6 hexadialdo 1,5 pyranose derivative 2 amino 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 thiadiazole 2 amino 5 [5' (alpha levo arabinopyranosyl)] 1,3,4 thiadiazole 2 amino 5 [5' (beta levo arabinopyranosyl)] 1,3,4 thiadiazole 2 methyl 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (alpha levo arabinofuranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (alpha levo arabinopyranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (beta levo arabinofuranosyl)] 1,3,4 oxadiazole 2 phenyl 5 [5' (beta levo arabinopyranosyl)] 1,3,4 oxadiazole 5 [5' (1',2':3',4' di o isopropylidene beta levo arabinopyranosyl)]tetrazole 5 [5' (alpha levo arabinopyranosyl)]tetrazole 5 [5' (beta levo arabinopyranosyl)]tetrazole functional group isocarbonucleoside derivatives isopropylidene n acetyl alpha dextro galacturonopyranosylhydrazide n acetyl beta dextro galacturonopyranosylhydrazide nucleoside derivative unclassified drug antiviral activity article assay carbon nuclear magnetic resonance deprotection reaction heating intermethod comparison microwave radiation proton nuclear magnetic resonance reaction time solubility |
| description |
Deprotection of 5-glycosyl heterocyclic derivatives of 1,2:3:4-di-O- isopropylidene-α-D-galacto-1,6-hexadialdo-1,5-pyranose allowed isocarbonucleoside analogues to be obtained with enhaced solubility in the aqueous medium used for antiviral assays. Looking for a deprotection method of isopropylidene groups which would not affect the heterocycle, we performed and compared different deprotection techniques using microwave radiation or thermal heating and found that, in most cases, this goal could be achieved, in short times and good yields, when the reactions were microwave-assisted. |
| format |
JOUR |
| author |
Martínez Esperón, M.F. Errea, M.I. Martins Alho, M.A. D'Accorso, N.B. |
| author_facet |
Martínez Esperón, M.F. Errea, M.I. Martins Alho, M.A. D'Accorso, N.B. |
| author_sort |
Martínez Esperón, M.F. |
| title |
Deprotection of di-O-isopropylidene isocarbonucleosides |
| title_short |
Deprotection of di-O-isopropylidene isocarbonucleosides |
| title_full |
Deprotection of di-O-isopropylidene isocarbonucleosides |
| title_fullStr |
Deprotection of di-O-isopropylidene isocarbonucleosides |
| title_full_unstemmed |
Deprotection of di-O-isopropylidene isocarbonucleosides |
| title_sort |
deprotection of di-o-isopropylidene isocarbonucleosides |
| url |
http://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p491_MartinezEsperon |
| work_keys_str_mv |
AT martinezesperonmf deprotectionofdioisopropylideneisocarbonucleosides AT erreami deprotectionofdioisopropylideneisocarbonucleosides AT martinsalhoma deprotectionofdioisopropylideneisocarbonucleosides AT daccorsonb deprotectionofdioisopropylideneisocarbonucleosides |
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1782026999962796032 |