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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| LEADER | 05284caa a22005417a 4500 | ||
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| 001 | PAPER-1068 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203025.0 | ||
| 008 | 190411s1985 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-46549091471 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a CRBRA | ||
| 100 | 1 | |a du Mortier, C. | |
| 245 | 1 | 0 | |a Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy |
| 260 | |c 1985 | ||
| 270 | 1 | 0 | |m du Mortier, C.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria Pabellon II, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a de Lederkremer, Sala, (1975) Carbohydr. Res., 40, pp. 385-386 | ||
| 504 | |a Varela, Fernández Cirelli, de Lederkremer, (1979) Carbohydr. Res., 70, pp. 27-35 | ||
| 504 | |a Sala, Fernández Cirelli, de Lederkremer, (1980) Carbohydr. Res., 78, pp. 61-66 | ||
| 504 | |a 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 | ||
| 504 | |a de Lederkremer, Litter, (1971) Carbohydr. Res., 20, pp. 442-444 | ||
| 504 | |a Varela, Fernández Cirelli, de Lederkremer, (1982) Carbohydr. Res., 100, pp. 424-430 | ||
| 504 | |a Slessor, Tracey, Couplings into Methylene Groups: a New Nuclear Magnetic Resonance Approach to Stereochemistry (1971) Canadian Journal of Chemistry, 49, pp. 2874-2884 | ||
| 504 | |a Hall, Black, Slessor, Tracey, Conformational Studies on the 1,2;5,6-Di-O-isopropylidene-D-hexoses (1972) Canadian Journal of Chemistry, 50, pp. 1912-1924 | ||
| 504 | |a Varela, Cirelli, de Lederkremer, A crystalline furanose derivative of ascarylose. Synthesis of 2,5-di-O-benzoyl-3,6-dideoxy-α-L-arabino-hexofuranose (1980) Carbohydrate Research, 85, pp. 130-135 | ||
| 504 | |a Cirelli, Sznaidman, Varela, de Lederkremer, (1983) Tetrahedron, 39, pp. 313-316 | ||
| 504 | |a Bock, Pedersen, (1983) Adv. Carbohydr. Chem. Biochem., 41, pp. 27-66 | ||
| 504 | |a Kohn, Samaritano, Lerner, (1965) J. Am. Chem. Soc., 87, pp. 5475-5480 | ||
| 504 | |a Stevens, Fletcher, Jr., (1968) J. Org. Chem., 33, pp. 1799-1805 | ||
| 504 | |a Gillard, Israel, (1981) Tetrahedron Lett., 22, pp. 513-516 | ||
| 504 | |a Gorin, Mazurek, Further Studies on the Assignment of Signals in13C Magnetic Resonance Spectra of Aldoses and Derived Methyl Glycosides (1975) Canadian Journal of Chemistry, 53, pp. 1212-1223 | ||
| 504 | |a Gorin, Mazurek, (1976) Carbohydr. Res., 48, pp. 171-186 | ||
| 504 | |a Wolfrom, Wood, Jr., (1949) J. Am. Chem. Soc., 71, pp. 3175-3176 | ||
| 520 | 3 | |a 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. |l eng | |
| 536 | |a Detalles de la financiación: Consejo De Ciencia, Innovación Y Tecnología Del Estado De Yucatán | ||
| 536 | |a Detalles de la financiación: We thank UMYMFOR-CONICET-FCEN (Unidad de Microanalisis y Metodos Fisicos Organicos, Consejo National de InvestigacionesC ientificas y Tecnicas Facultad de Ciencias Exactas y Naturales) for the microanalysesa nd spectra and SUBCYT (Subsecretariad e Estado de Ciencia y Tecnologia) for financials upport. | ||
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria Pabellon II, 1428 Buenos Aires, Argentina | ||
| 700 | 1 | |a de Lederkremer, R.M. | |
| 773 | 0 | |d 1985 |g v. 139 |h pp. 47-54 |k n. C |p Carbohydr. Res. |x 00086215 |w (AR-BaUEN)CENRE-301 |t Carbohydrate Research | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/0008-6215(85)90005-9 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00086215_v139_nC_p47_duMortier |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v139_nC_p47_duMortier |y Registro en la Biblioteca Digital |
| 961 | |a paper_00086215_v139_nC_p47_duMortier |b paper |c PE | ||
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| 963 | |a VARI | ||
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