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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Autores principales: Cicero, Daniel Oscar, Varela, Oscar José, Muchnik de Lederkremer, Rosa María
Publicado: 1990
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v46_n4_p1131_Cicero
http://hdl.handle.net/20.500.12110/paper_00404020_v46_n4_p1131_Cicero
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling paper:paper_00404020_v46_n4_p1131_Cicero2023-06-08T15:04:11Z Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose Cicero, Daniel Oscar Varela, Oscar José Muchnik de Lederkremer, Rosa María 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. 1990 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v46_n4_p1131_Cicero 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.
author Cicero, Daniel Oscar
Varela, Oscar José
Muchnik de Lederkremer, Rosa María
spellingShingle Cicero, Daniel Oscar
Varela, Oscar José
Muchnik de Lederkremer, Rosa María
Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose
author_facet Cicero, Daniel Oscar
Varela, Oscar José
Muchnik de Lederkremer, Rosa María
author_sort Cicero, Daniel Oscar
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
publishDate 1990
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v46_n4_p1131_Cicero
http://hdl.handle.net/20.500.12110/paper_00404020_v46_n4_p1131_Cicero
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AT varelaoscarjose synthesisoffuranoidandpyranoidderivativesof6deoxy4thiodgalactose
AT muchnikdelederkremerrosamaria synthesisoffuranoidandpyranoidderivativesof6deoxy4thiodgalactose
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