Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy

Debenzoylation of 2,4,6-tri-O-benzoyl-3-deoxy-d-arabino-hexono-1,5-lactone (1) followed by heating in vacuo and rebenzoylation afforded 2,5,6-tri-O-benzoyl-3-deoxy-d-arabino-hexono-1,4-lactone (2). Reduction of 2 with disiamylborane gave 2,5,6-tri-O-benzoyl-3-deoxy-d-arabino-hexofuranose (3), a conv...

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Autores principales: du Mortier, C., de Lederkremer, R.M.
Formato: JOUR
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00086215_v139_nC_p47_duMortier
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_00086215_v139_nC_p47_duMortier2023-10-03T14:06:20Z Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy du Mortier, C. de Lederkremer, R.M. Debenzoylation of 2,4,6-tri-O-benzoyl-3-deoxy-d-arabino-hexono-1,5-lactone (1) followed by heating in vacuo and rebenzoylation afforded 2,5,6-tri-O-benzoyl-3-deoxy-d-arabino-hexono-1,4-lactone (2). Reduction of 2 with disiamylborane gave 2,5,6-tri-O-benzoyl-3-deoxy-d-arabino-hexofuranose (3), a convenient furanose derivative for the synthesis of glycosides. Acetylation of 3 with acetic anhydride-pyridine afforded 1-O-acetyl-2,5,6-tri-O-benzoyl-3-deoxy-α-d-arabino-hexofuranose (4). Compound 4 was converted into methyl 2,4,6-tri-O-benzoyl-3-deoxy-α-d-arabino-hexofuranoside (5) through the bromide obtained by treatment of 4 with bromotrimethylsilane, followed by methanol. Debenzoylation of 5 gave methyl 3-deoxy-α-d-arabino-hexofuranoside (6). All compounds mentioned were obtained crystalline. Conformational studies of 4, 5, and 6 were made by 1H-n.m.r. spectroscopy (DAERM method), and the 13C-n.m.r. spectral data are correlated. The structures of compounds 2, 4 and 5 were also confirmed by mass spectrometry. {A figure is presented}. © 1985. 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_v139_nC_p47_duMortier
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
description Debenzoylation of 2,4,6-tri-O-benzoyl-3-deoxy-d-arabino-hexono-1,5-lactone (1) followed by heating in vacuo and rebenzoylation afforded 2,5,6-tri-O-benzoyl-3-deoxy-d-arabino-hexono-1,4-lactone (2). Reduction of 2 with disiamylborane gave 2,5,6-tri-O-benzoyl-3-deoxy-d-arabino-hexofuranose (3), a convenient furanose derivative for the synthesis of glycosides. Acetylation of 3 with acetic anhydride-pyridine afforded 1-O-acetyl-2,5,6-tri-O-benzoyl-3-deoxy-α-d-arabino-hexofuranose (4). Compound 4 was converted into methyl 2,4,6-tri-O-benzoyl-3-deoxy-α-d-arabino-hexofuranoside (5) through the bromide obtained by treatment of 4 with bromotrimethylsilane, followed by methanol. Debenzoylation of 5 gave methyl 3-deoxy-α-d-arabino-hexofuranoside (6). All compounds mentioned were obtained crystalline. Conformational studies of 4, 5, and 6 were made by 1H-n.m.r. spectroscopy (DAERM method), and the 13C-n.m.r. spectral data are correlated. The structures of compounds 2, 4 and 5 were also confirmed by mass spectrometry. {A figure is presented}. © 1985.
format JOUR
author du Mortier, C.
de Lederkremer, R.M.
spellingShingle du Mortier, C.
de Lederkremer, R.M.
Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy
author_facet du Mortier, C.
de Lederkremer, R.M.
author_sort du Mortier, C.
title Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy
title_short Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy
title_full Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy
title_fullStr Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy
title_full_unstemmed Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy
title_sort crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: conformational studies by n.m.r. spectroscopy
url http://hdl.handle.net/20.500.12110/paper_00086215_v139_nC_p47_duMortier
work_keys_str_mv AT dumortierc crystallinefuranosederivativesof3deoxydarabinohexoseconformationalstudiesbynmrspectroscopy
AT delederkremerrm crystallinefuranosederivativesof3deoxydarabinohexoseconformationalstudiesbynmrspectroscopy
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