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...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Sznaidman, M.L., Cirelli, A.F., de Lederkremer, R.M.
Formato: JOUR
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00086215_v146_n2_p233_Sznaidman
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00086215_v146_n2_p233_Sznaidman
record_format dspace
spelling todo:paper_00086215_v146_n2_p233_Sznaidman2023-10-03T14:06:21Z Synthesis of 5-O-methyl-d-galactofuranose Sznaidman, M.L. Cirelli, A.F. de Lederkremer, R.M. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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.
format JOUR
author Sznaidman, M.L.
Cirelli, A.F.
de Lederkremer, R.M.
spellingShingle Sznaidman, M.L.
Cirelli, A.F.
de Lederkremer, R.M.
Synthesis of 5-O-methyl-d-galactofuranose
author_facet Sznaidman, M.L.
Cirelli, A.F.
de Lederkremer, R.M.
author_sort Sznaidman, M.L.
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
url http://hdl.handle.net/20.500.12110/paper_00086215_v146_n2_p233_Sznaidman
work_keys_str_mv AT sznaidmanml synthesisof5omethyldgalactofuranose
AT cirelliaf synthesisof5omethyldgalactofuranose
AT delederkremerrm synthesisof5omethyldgalactofuranose
_version_ 1807316326697402368

Ejemplares similares