Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose
Benzoylation ofD-glycero-D-gulo-heptono-1,4-lactone afforded 2,3,5,6,7-penta-O-benzoyl-D-glycero-D-gulo-heptono-1,4-lactone, which, by 3-deoxygenation, gave 2,5,6,7-tetra-O-benzoyl-3-deoxy-D-gluco-heptono-1,4-lactone (4) in 80% overall yield. In a similar way, 2,5,6,7-tetra-O-acetyl-3-deoxy-D-gluco-...
Guardado en:
| Autor principal: | |
|---|---|
| Otros Autores: | , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
1987
|
| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 05697caa a22005777a 4500 | ||
|---|---|---|---|
| 001 | PAPER-874 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203013.0 | ||
| 008 | 190411s1987 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-33646901243 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a CRBRA | ||
| 100 | 1 | |a Jeroncic, L.O. | |
| 245 | 1 | 0 | |a Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose |
| 260 | |c 1987 | ||
| 270 | 1 | 0 | |m Jeroncic, L.O.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires. Ciudad Universitaria, Pabellón 2, piso 3, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Samuelsson, Lindberg, Brubaker, (1974) J. Bacteriol., 117, pp. 1010-1016 | ||
| 504 | |a Hoffman, Lindberg, Skaug, Hofstad, (1980) Carbohydr. Res., 84, pp. 181-183 | ||
| 504 | |a Varela, Fernández 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 Du Mortier, de Lederkremer, (1985) Carbohydr. Res., 139, pp. 47-54 | ||
| 504 | |a Litter, de Lederkremer, (1973) Carbohydr. Res., 26, pp. 431-434 | ||
| 504 | |a Varela, Fernández Cirelli, de Lederkremer, (1982) Carbohydr. Res., 100, pp. 424-430 | ||
| 504 | |a Jeroncic, Varela, Fernández Cirelli, de Lederkremer, (1984) Tetrahedron, 40, pp. 1425-1430 | ||
| 504 | |a Bock, Lundt, Pedersen, Preparation of 3-Deoxyaldonolactones by Hydrogenolysis of Acetylated Aldonolactones. (1981) Acta Chemica Scandinavica, 35, pp. 155-162 | ||
| 504 | |a Sala, Fernández Cirelli, de Lederkremer, (1980) Carbohydr. Res., 78, pp. 61-66 | ||
| 504 | |a Kohn, Samaritano, Lerner, (1966) J. Org. Chem., 31, pp. 1503-1506 | ||
| 504 | |a Fernández Cirelli, Sznaidman, Verela, de Lederkremer, (1983) Tetrahedron, 39, pp. 313-316 | ||
| 504 | |a Bock, Pedersen, (1983) Adv. Carbohydr. Chem. Biochem., 41, pp. 27-66 | ||
| 504 | |a Sznaidman, Fernández Cirelli, de Lederkremer, 13C NMR Spectral Studies of Di- and Trideoxyaldohexoses (1986) Journal of Carbohydrate Chemistry, 5, pp. 249-255 | ||
| 504 | |a Mastronardi, Flematti, Deferrari, Gros, (1966) Carbohydr. Res., 3, pp. 177-183 | ||
| 504 | |a Hanessian, Banoub, (1977) Carbohydr. Res., 59, pp. 261-267 | ||
| 504 | |a Dyong, Baumeister, Bendlin, (1979) Chem. Ber., 112, pp. 161-174 | ||
| 504 | |a Pfeffer, Parrish, Unruh, Effects of carbohydrate-structure changes on induced shifts in differential isotope-shift 13C-N.M.R. (1980) Carbohydrate Research, 84, pp. 13-23 | ||
| 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 Trevelyan, Procter, Harrison, (1950) Nature (London), 166, pp. 444-445 | ||
| 504 | |a Kohn, Samaritano, Lerner, (1965) J. Am. Chem. Soc., 87, pp. 5475-5480 | ||
| 520 | 3 | |a Benzoylation ofD-glycero-D-gulo-heptono-1,4-lactone afforded 2,3,5,6,7-penta-O-benzoyl-D-glycero-D-gulo-heptono-1,4-lactone, which, by 3-deoxygenation, gave 2,5,6,7-tetra-O-benzoyl-3-deoxy-D-gluco-heptono-1,4-lactone (4) in 80% overall yield. In a similar way, 2,5,6,7-tetra-O-acetyl-3-deoxy-D-gluco-heptono-1,4-lactone was prepared. Disiamylborane reduction of compound 4 gave crystalline 2,5,6,7-tetra-O-benzoyl-3-deoxy-β-D-gluco-heptofuranose (6), which was acetylated to give crystalline 1-O-acetyl-2,5,6,7-tetra-O-benzoyl-3-deoxy-β-D-gluco-heptofuranose (7). Upon treatment of 6 with diazomethane-boron trifluoride etherate, methyl 2,5,6,7-tetra-O-benzoyl-3-deoxy-β-D-gluco-heptofuranoside (8) was obtained. From the reaction mixture, the benzoylated β,β′-furanosyl disaccharide 11 was isolated. A higher yield (90%) of 8 was obtained by treatment of 7 with methanol and tin(IV) chloride. On O-debenzoylation of 8, methyl 3-deoxy-β-D-gluco-heptofuranoside was obtained. Compound 11 was the sole product (82% yield) when 6 was treated with boron trifluoride-etherate in dichloromethane. O-Debenzoylation of 11 afforded crystalline 3-deoxy-β-D-gluco-heptofuranosyl 3-deoxy-β-D-gluco-heptofuranoside. O-Debenzoylation of 6 with sodium methoxide in chloroform afforded crystalline 3-deoxy-D-gluco-heptose, whose tautomeric equilibrium was studied by 13C-n.m.r. spectroscopy. © 1987. |l eng | |
| 536 | |a Detalles de la financiación: We thank CONICET (Consejo National de Investigaciones Cientificas y TCcnicas) for financial support, and UMYMFOR (.CONICET-FCEN, Buenos Aires) for the microanalyses and spectra. | ||
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires. Ciudad Universitaria, Pabellón 2, piso 3, 1428 Buenos Aires, Argentina | ||
| 700 | 1 | |a Cirelli, A.F. | |
| 700 | 1 | |a de Lederkremer, R.M. | |
| 773 | 0 | |d 1987 |g v. 167 |h pp. 175-186 |k n. C |p Carbohydr. Res. |x 00086215 |w (AR-BaUEN)CENRE-301 |t Carbohydrate Research | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-33646901243&doi=10.1016%2f0008-6215%2887%2980277-X&partnerID=40&md5=8fa908f2ac4b0b6c2f1437b902577f65 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/0008-6215(87)80277-X |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00086215_v167_nC_p175_Jeroncic |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v167_nC_p175_Jeroncic |y Registro en la Biblioteca Digital |
| 961 | |a paper_00086215_v167_nC_p175_Jeroncic |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 61827 | ||