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Abstract:

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.

Registro:

Documento: Artículo
Título:Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy
Autor:du Mortier, C.; de Lederkremer, R.M.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria Pabellon II, 1428 Buenos Aires, Argentina
Año:1985
Volumen:139
Número:C
Página de inicio:47
Página de fin:54
DOI: http://dx.doi.org/10.1016/0008-6215(85)90005-9
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v139_nC_p47_duMortier

Referencias:

  • de Lederkremer, Sala, (1975) Carbohydr. Res., 40, pp. 385-386
  • Varela, Fernández Cirelli, de Lederkremer, (1979) Carbohydr. Res., 70, pp. 27-35
  • Sala, Fernández Cirelli, de Lederkremer, (1980) Carbohydr. Res., 78, pp. 61-66
  • du Mortier, de Lederkremer, A New Synthesis of 3-Deoxy-D-arabino-hexose and its Tautomeric Equilibrium (1984) Journal of Carbohydrate Chemistry, 3, pp. 219-228
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  • Varela, Fernández Cirelli, de Lederkremer, (1982) Carbohydr. Res., 100, pp. 424-430
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Citas:

---------- APA ----------
du Mortier, C. & de Lederkremer, R.M. (1985) . Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy. Carbohydrate Research, 139(C), 47-54.
http://dx.doi.org/10.1016/0008-6215(85)90005-9
---------- CHICAGO ----------
du Mortier, C., de Lederkremer, R.M. "Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy" . Carbohydrate Research 139, no. C (1985) : 47-54.
http://dx.doi.org/10.1016/0008-6215(85)90005-9
---------- MLA ----------
du Mortier, C., de Lederkremer, R.M. "Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy" . Carbohydrate Research, vol. 139, no. C, 1985, pp. 47-54.
http://dx.doi.org/10.1016/0008-6215(85)90005-9
---------- VANCOUVER ----------
du Mortier, C., de Lederkremer, R.M. Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy. Carbohydr. Res. 1985;139(C):47-54.
http://dx.doi.org/10.1016/0008-6215(85)90005-9