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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1986
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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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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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1768541638515228672 |