Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose
The synthesis of pyranoid and furanoid derivatives of 6-deoxy-4-thio-D-galactose from methyl α-D-glucopyranoside (1) is described. A key intermediate for the synthesis, methyl 2,3-di-O-benzoyl-6-deoxy-4-thio-α-D-galactopyranoside (15) was prepared by different approaches from 1. Regioselectivity for...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00404020_v46_n4_p1131_Cicero |
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todo:paper_00404020_v46_n4_p1131_Cicero2023-10-03T14:50:35Z Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose Cicero, D. Varela, O. De Lederkremer, R.M. The synthesis of pyranoid and furanoid derivatives of 6-deoxy-4-thio-D-galactose from methyl α-D-glucopyranoside (1) is described. A key intermediate for the synthesis, methyl 2,3-di-O-benzoyl-6-deoxy-4-thio-α-D-galactopyranoside (15) was prepared by different approaches from 1. Regioselectivity for the protection or modification of the hydroxyl groups of 1 or its derivatives was achieved by employing various reagents. The thiol group at C-4 was introduced by nucleophilic substitution of a tosylate by thiocyanate followed by reduction or alkaline methanolysis of the thiocyano group. A by-product of the latter reaction was characterized as a monothiolcarbonate derivative (17), whose conformation was studied by molecular mechanics calculations. Acetolysis of methyl 6-deoxy-4-thio-α-D-galactopyranoside (16) afforded ring sulfur containing derivatives of 6-deoxy-4-thio-D-galactofuranose, which are described for the first time. © 1990. Fil:Cicero, D. 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. Fil:De Lederkremer, R.M. 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_00404020_v46_n4_p1131_Cicero |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
The synthesis of pyranoid and furanoid derivatives of 6-deoxy-4-thio-D-galactose from methyl α-D-glucopyranoside (1) is described. A key intermediate for the synthesis, methyl 2,3-di-O-benzoyl-6-deoxy-4-thio-α-D-galactopyranoside (15) was prepared by different approaches from 1. Regioselectivity for the protection or modification of the hydroxyl groups of 1 or its derivatives was achieved by employing various reagents. The thiol group at C-4 was introduced by nucleophilic substitution of a tosylate by thiocyanate followed by reduction or alkaline methanolysis of the thiocyano group. A by-product of the latter reaction was characterized as a monothiolcarbonate derivative (17), whose conformation was studied by molecular mechanics calculations. Acetolysis of methyl 6-deoxy-4-thio-α-D-galactopyranoside (16) afforded ring sulfur containing derivatives of 6-deoxy-4-thio-D-galactofuranose, which are described for the first time. © 1990. |
| format |
JOUR |
| author |
Cicero, D. Varela, O. De Lederkremer, R.M. |
| spellingShingle |
Cicero, D. Varela, O. De Lederkremer, R.M. Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose |
| author_facet |
Cicero, D. Varela, O. De Lederkremer, R.M. |
| author_sort |
Cicero, D. |
| title |
Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose |
| title_short |
Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose |
| title_full |
Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose |
| title_fullStr |
Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose |
| title_full_unstemmed |
Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose |
| title_sort |
synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-d-galactose |
| url |
http://hdl.handle.net/20.500.12110/paper_00404020_v46_n4_p1131_Cicero |
| work_keys_str_mv |
AT cicerod synthesisoffuranoidandpyranoidderivativesof6deoxy4thiodgalactose AT varelao synthesisoffuranoidandpyranoidderivativesof6deoxy4thiodgalactose AT delederkremerrm synthesisoffuranoidandpyranoidderivativesof6deoxy4thiodgalactose |
| _version_ |
1807321659753889792 |