Synthesis of 5-O-methyl-d-galactofuranose

5-O-Methyl-d-galactofuranose (7) was synthesized, for the first time, in five steps from d-galactono-1,4-lactone (1) in good overall yield. Tritylation and further acetylation of 1 gave 2,3,5-tri-O-acetyl-6-O-trityl-d-galactono-1,4-lactone (2); prolonged acetylation caused elimination to form 2,5-di...

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Autores principales: Sznaidman, Marcos Luis, Muchnik de Lederkremer, Rosa María
Publicado: 1986
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v146_n2_p233_Sznaidman
http://hdl.handle.net/20.500.12110/paper_00086215_v146_n2_p233_Sznaidman
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spelling paper:paper_00086215_v146_n2_p233_Sznaidman2023-06-08T14:32:15Z Synthesis of 5-O-methyl-d-galactofuranose Sznaidman, Marcos Luis Muchnik de Lederkremer, Rosa María 5-O-Methyl-d-galactofuranose (7) was synthesized, for the first time, in five steps from d-galactono-1,4-lactone (1) in good overall yield. Tritylation and further acetylation of 1 gave 2,3,5-tri-O-acetyl-6-O-trityl-d-galactono-1,4-lactone (2); prolonged acetylation caused elimination to form 2,5-di-O-acetyl-3-deoxy-6-O-trityl-d-threo-hex-2-enono-1,4-lactone. Detritylation of 2 with BF3 · Et2O occurred with acetyl migration and afforded 2,3,6-tri-O-acetyl-d-galactono-1,4-lactone (4). Methylation of 4 with CH2N2BF3 · Et2O gave 5-O-methyl-2,3,6-tri-O-acetyl-d-galactono-1,4-lactone. Subsequent reduction by disiamylborane followed by controlled deacetylation gave crystalline 7. The 1H- and 13C-n.m.r. spectra of 7 indicated a 1:1.3 ratio of the α and β furanose anomers. © 1986. Fil:Sznaidman, M.L. 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. 1986 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v146_n2_p233_Sznaidman http://hdl.handle.net/20.500.12110/paper_00086215_v146_n2_p233_Sznaidman
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
description 5-O-Methyl-d-galactofuranose (7) was synthesized, for the first time, in five steps from d-galactono-1,4-lactone (1) in good overall yield. Tritylation and further acetylation of 1 gave 2,3,5-tri-O-acetyl-6-O-trityl-d-galactono-1,4-lactone (2); prolonged acetylation caused elimination to form 2,5-di-O-acetyl-3-deoxy-6-O-trityl-d-threo-hex-2-enono-1,4-lactone. Detritylation of 2 with BF3 · Et2O occurred with acetyl migration and afforded 2,3,6-tri-O-acetyl-d-galactono-1,4-lactone (4). Methylation of 4 with CH2N2BF3 · Et2O gave 5-O-methyl-2,3,6-tri-O-acetyl-d-galactono-1,4-lactone. Subsequent reduction by disiamylborane followed by controlled deacetylation gave crystalline 7. The 1H- and 13C-n.m.r. spectra of 7 indicated a 1:1.3 ratio of the α and β furanose anomers. © 1986.
author Sznaidman, Marcos Luis
Muchnik de Lederkremer, Rosa María
spellingShingle Sznaidman, Marcos Luis
Muchnik de Lederkremer, Rosa María
Synthesis of 5-O-methyl-d-galactofuranose
author_facet Sznaidman, Marcos Luis
Muchnik de Lederkremer, Rosa María
author_sort Sznaidman, Marcos Luis
title Synthesis of 5-O-methyl-d-galactofuranose
title_short Synthesis of 5-O-methyl-d-galactofuranose
title_full Synthesis of 5-O-methyl-d-galactofuranose
title_fullStr Synthesis of 5-O-methyl-d-galactofuranose
title_full_unstemmed Synthesis of 5-O-methyl-d-galactofuranose
title_sort synthesis of 5-o-methyl-d-galactofuranose
publishDate 1986
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v146_n2_p233_Sznaidman
http://hdl.handle.net/20.500.12110/paper_00086215_v146_n2_p233_Sznaidman
work_keys_str_mv AT sznaidmanmarcosluis synthesisof5omethyldgalactofuranose
AT muchnikdelederkremerrosamaria synthesisof5omethyldgalactofuranose
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