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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1985
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v139_nC_p47_duMortier http://hdl.handle.net/20.500.12110/paper_00086215_v139_nC_p47_duMortier |
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paper:paper_00086215_v139_nC_p47_duMortier2023-06-08T14:32:14Z Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy Muchnik de Lederkremer, Rosa María 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. 1985 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v139_nC_p47_duMortier 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. |
| author |
Muchnik de Lederkremer, Rosa María |
| spellingShingle |
Muchnik de Lederkremer, Rosa María Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy |
| author_facet |
Muchnik de Lederkremer, Rosa María |
| author_sort |
Muchnik de Lederkremer, Rosa María |
| 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 |
| publishDate |
1985 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v139_nC_p47_duMortier http://hdl.handle.net/20.500.12110/paper_00086215_v139_nC_p47_duMortier |
| work_keys_str_mv |
AT muchnikdelederkremerrosamaria crystallinefuranosederivativesof3deoxydarabinohexoseconformationalstudiesbynmrspectroscopy |
| _version_ |
1768544532020854784 |