Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs
Methanolysis of 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone gave methyl 3-bromo-3-deoxy-2,4,6-tri-O-benzoyl-α-D-ribo-hex-2-ulofuranosonate (3) and the anomeric mixture of the analogous 4,6-di-O-benzoyl derivative, having HO-2 free. Compound 3 was subjected to debromination with tri...
Guardado en:
| Autores principales: | , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v328_n4_p605_DiNardo |
| Aporte de: |
| id |
todo:paper_00086215_v328_n4_p605_DiNardo |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_00086215_v328_n4_p605_DiNardo2023-10-03T14:06:56Z Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs Di Nardo, C. Varela, O. 3-Deoxy-D-erythro-2-hexulosonic acid 3-Deuterio derivatives Aldonolactones Furanose derivatives of 3-deoxy-2-hexulosonic acid Methanolysis 3 deoxy dextro erythro 2 hexulosonic acid derivative furan derivative lactone derivative methyl 3 bromo 3 deoxy 2,4,6 tri o benzoyl alpha dextro ribo hex 2 ulofuranosonic acid methyl 3 bromo 3 deoxy 4,6 di o benzoyl alpha,beta dextro ribo hex 2 ulofuranosonic acid methyl 3 deoxy 3 deutero 2,4,6 tri o benzoyl alpha dextro arabino hex 2 ulofuranosonic acid methyl 3 deoxy 3 deutero 2,4,6 tri o benzoyl alpha dextro ribo hex 2 ulofuranosonic acid nitrile tributyltin unclassified drug article carbohydrate synthesis chemical structure debromination degradation priority journal reaction analysis structure analysis Bacteria Furans Gluconates Ketoses Sugar Acids Support, Non-U.S. Gov't Methanolysis of 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone gave methyl 3-bromo-3-deoxy-2,4,6-tri-O-benzoyl-α-D-ribo-hex-2-ulofuranosonate (3) and the anomeric mixture of the analogous 4,6-di-O-benzoyl derivative, having HO-2 free. Compound 3 was subjected to debromination with tributyltin hydride and tributyltin deuteride in the presence of 2,2'-azo-bisisobutyronitrile affording, respectively, the corresponding derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and its 3-deuterio analog. The structure of the products and intermediates was established by spectroscopic methods and chemical transformations. (C) 2000 Elsevier Science Ltd. Fil:Di Nardo, C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, 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_00086215_v328_n4_p605_DiNardo |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
3-Deoxy-D-erythro-2-hexulosonic acid 3-Deuterio derivatives Aldonolactones Furanose derivatives of 3-deoxy-2-hexulosonic acid Methanolysis 3 deoxy dextro erythro 2 hexulosonic acid derivative furan derivative lactone derivative methyl 3 bromo 3 deoxy 2,4,6 tri o benzoyl alpha dextro ribo hex 2 ulofuranosonic acid methyl 3 bromo 3 deoxy 4,6 di o benzoyl alpha,beta dextro ribo hex 2 ulofuranosonic acid methyl 3 deoxy 3 deutero 2,4,6 tri o benzoyl alpha dextro arabino hex 2 ulofuranosonic acid methyl 3 deoxy 3 deutero 2,4,6 tri o benzoyl alpha dextro ribo hex 2 ulofuranosonic acid nitrile tributyltin unclassified drug article carbohydrate synthesis chemical structure debromination degradation priority journal reaction analysis structure analysis Bacteria Furans Gluconates Ketoses Sugar Acids Support, Non-U.S. Gov't |
| spellingShingle |
3-Deoxy-D-erythro-2-hexulosonic acid 3-Deuterio derivatives Aldonolactones Furanose derivatives of 3-deoxy-2-hexulosonic acid Methanolysis 3 deoxy dextro erythro 2 hexulosonic acid derivative furan derivative lactone derivative methyl 3 bromo 3 deoxy 2,4,6 tri o benzoyl alpha dextro ribo hex 2 ulofuranosonic acid methyl 3 bromo 3 deoxy 4,6 di o benzoyl alpha,beta dextro ribo hex 2 ulofuranosonic acid methyl 3 deoxy 3 deutero 2,4,6 tri o benzoyl alpha dextro arabino hex 2 ulofuranosonic acid methyl 3 deoxy 3 deutero 2,4,6 tri o benzoyl alpha dextro ribo hex 2 ulofuranosonic acid nitrile tributyltin unclassified drug article carbohydrate synthesis chemical structure debromination degradation priority journal reaction analysis structure analysis Bacteria Furans Gluconates Ketoses Sugar Acids Support, Non-U.S. Gov't Di Nardo, C. Varela, O. Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs |
| topic_facet |
3-Deoxy-D-erythro-2-hexulosonic acid 3-Deuterio derivatives Aldonolactones Furanose derivatives of 3-deoxy-2-hexulosonic acid Methanolysis 3 deoxy dextro erythro 2 hexulosonic acid derivative furan derivative lactone derivative methyl 3 bromo 3 deoxy 2,4,6 tri o benzoyl alpha dextro ribo hex 2 ulofuranosonic acid methyl 3 bromo 3 deoxy 4,6 di o benzoyl alpha,beta dextro ribo hex 2 ulofuranosonic acid methyl 3 deoxy 3 deutero 2,4,6 tri o benzoyl alpha dextro arabino hex 2 ulofuranosonic acid methyl 3 deoxy 3 deutero 2,4,6 tri o benzoyl alpha dextro ribo hex 2 ulofuranosonic acid nitrile tributyltin unclassified drug article carbohydrate synthesis chemical structure debromination degradation priority journal reaction analysis structure analysis Bacteria Furans Gluconates Ketoses Sugar Acids Support, Non-U.S. Gov't |
| description |
Methanolysis of 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone gave methyl 3-bromo-3-deoxy-2,4,6-tri-O-benzoyl-α-D-ribo-hex-2-ulofuranosonate (3) and the anomeric mixture of the analogous 4,6-di-O-benzoyl derivative, having HO-2 free. Compound 3 was subjected to debromination with tributyltin hydride and tributyltin deuteride in the presence of 2,2'-azo-bisisobutyronitrile affording, respectively, the corresponding derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and its 3-deuterio analog. The structure of the products and intermediates was established by spectroscopic methods and chemical transformations. (C) 2000 Elsevier Science Ltd. |
| format |
JOUR |
| author |
Di Nardo, C. Varela, O. |
| author_facet |
Di Nardo, C. Varela, O. |
| author_sort |
Di Nardo, C. |
| title |
Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs |
| title_short |
Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs |
| title_full |
Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs |
| title_fullStr |
Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs |
| title_full_unstemmed |
Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs |
| title_sort |
synthesis of furanose derivatives of 3-deoxy-d-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v328_n4_p605_DiNardo |
| work_keys_str_mv |
AT dinardoc synthesisoffuranosederivativesof3deoxyderythro2hexulosonicacidandtheir3bromoand3deuterioanalogs AT varelao synthesisoffuranosederivativesof3deoxyderythro2hexulosonicacidandtheir3bromoand3deuterioanalogs |
| _version_ |
1782029423987392512 |