Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end

Mostrar otras versiones (1)

Thiodisaccharides having a 1-thiopentofuranose nonreducing end were synthesized by two routes starting from per-O-acylaldofuranoses with arabino, ribo, and xylo configurations. These glycosyl donors were converted into S-glycosyl isothiourea derivatives as precursors of 1-thiofuranose units, which w...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autor principal: Repetto, E.
Otros Autores: Marino, C., Uhrig, M.L, Varela, O.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2008
Acceso en línea:Registro en Scopus
DOI
Handle
Registro en la Biblioteca Digital
Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
LEADER 05587caa a22007577a 4500
001 PAPER-22458
003 AR-BaUEN
005 20230518205401.0
008 190411s2008 xx ||||fo|||| 00| 0 eng|d
024 7 |2 scopus  |a 2-s2.0-38849181001 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a EJOCF 
100 1 |a Repetto, E. 
245 1 0 |a Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as the nonreducing end 
260 |c 2008 
270 1 0 |m Varela, O.; CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: varela@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Driguez, H., (2001) ChemBioChem, 2, pp. 311-318 
504 |a Driguez, H., (1997) Top. Curr. Chem, 187, pp. 85-116 
504 |a Nicotra, F., (1997) Top. Curr. Chem, 187, pp. 55-83 
504 |a Szilágyi, L., Varela, O., (2006) Curr. Org. Chem, 10, pp. 1745-1770 
504 |a Pachamuthu, K., Schmidt, R.R., (2006) Chem. Rev, 106, pp. 160-187 
504 |a Turnbull, W.B., Field, R.A., (2000) J. Chem. Soc. Perkin Trans. 1, pp. 1859-1866 
504 |a Buckingham, J., Brazier, J.A., Fisher, J., Cosstick, R., (2007) Carbohydr. Res, 342, pp. 16-22 
504 |a Randell, K.D., Johnston, B.D., Lee, E.E., Pinto, B.M., (2000) Tetrahedron: Asymmetry, 11, pp. 207-222 
504 |a Minic, Z., Do, C.-T., Rihouey, C., Morin, H., Lerouge, P., Jouanin, L., (2006) J. Exp. Bot, 57, pp. 2339-2351 
504 |a Houseknecht, J.B., Lowary, T.L., (2001) Curr. Opin. Chem. Biol, 5, pp. 677-682 
504 |a Lopez, G., Daniellou, R., O'Donohue, M., Ferrières, V., Nugier-Chauvin, C., (2007) Bioorg. Med. Chem. Lett, 17, pp. 434-438 
504 |a Uhrig, M.L., Manzano, V.E., Varela, O., (2006) Eur. J. Org. Chem, pp. 162-168 
504 |a Marino, C., Mariño, K., Miletti, L., Manso Alves, M.J., Colli, W., Lederkremer, R.M., (1998) Glycobiology, 8, pp. 901-904 
504 |a Uhrig, M.L., Szilágyi, L., Kovér, K.E., Varela, O., (2007) Carbohydr. Res, 342, pp. 1841-1849 
504 |a Witczak, Z.J., Sun, J., Mielguj, R., (1995) Bioorg. Med. Chem. Lett, 5, pp. 2169-2174 
504 |a Witczak, Z.J., Chhabra, R., Chen, H., Xie, X.-Q., (1997) Carbohydr. Res, 301, pp. 167-175 
504 |a Witczak, Z.J., Kaplon, P., Kolodziej, M., (2002) Monatsh. Chem, 133, pp. 521-530 
504 |a Witczak, Z.J., Kaplon, P., Dey, P.M., (2003) Carbohydr. Res, 338, pp. 11-18 
504 |a Becker, B., Thimm, J., Thiem, J., (1996) J. Carbohydr. Chem, 15, pp. 1179-1181 
504 |a Horton, D., (1963) Methods Carbohydr. Chem, 2, pp. 433-437 
504 |a Horton, D., Wolfrom, M.L., (1962) J. Org. Chem, 27, pp. 1794-1800 
504 |a Ibatullin, F.M., Selivanov, S.I., Shavva, A.G., (2001) Synthesis, 3, pp. 419-422 
504 |a Ibatullin, F.M., Shabalin, K.A., Jänis, J.V., Shavva, A.G., (2003) Tetrahedron Lett, 44, pp. 7961-7964 
504 |a Gandolfi-Donadío, L., Gallo-Rodriguez, C., Lederkremer, R.M., (2006) Can. J. Chem, 84, pp. 486-491 
504 |a Gadikota, R.R., Callam, C.S., Wagner, T., Del Fraino, B., Lowary, T.L., (2003) J. Am. Chem. Soc, 125, pp. 4155-4165 
504 |a Szekeres, G.L., Bardos, T.J., (1972) J. Med. Chem, 15, pp. 1333-1334 
504 |a Rosemeyer, H., Tóth, G., Golankiewicz, B., Kazimierczuk, Z., Bourgeois, W., Kretschmer, U., Muth, H.-P., Seela, F., (1990) J. Org. Chem, 55, pp. 5784-5790 
504 |a Sherry, B.D., Loy, R.N., Toste, F.D., (2004) J. Am. Chem. Soc, 126, pp. 4510-4511 
504 |a Weng, S.-S., Lin, Y.-D., Chen, C.-T., (2006) Org. Lett, 8, pp. 5633-5636 
504 |a Martins Alho, M.A., D'Accorso, N.B., Thiel, I.M.E., (1996) J. Hetero cycl. Chem, 33, pp. 1339-1343 
520 3 |a Thiodisaccharides having a 1-thiopentofuranose nonreducing end were synthesized by two routes starting from per-O-acylaldofuranoses with arabino, ribo, and xylo configurations. These glycosyl donors were converted into S-glycosyl isothiourea derivatives as precursors of 1-thiofuranose units, which were generated in situ and trapped by a sugar enone to produce, by Michael addition, the thioglycosidic linkage. Alternatively, the MoO2Cl 2-promoted glycosylation of the thiol group of 6-thiosugar derivatives by per-O-acylfuranose led to thiodisaccharides with exclusive 1,2-trans diastereocontrol. © Wiley-VCH Verlag GmbH & Co. KGaA.  |l eng 
593 |a CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
690 1 0 |a CATALYSIS 
690 1 0 |a FURANOSE 
690 1 0 |a GLYCOSYLATION 
690 1 0 |a MICHAEL ADDITION 
690 1 0 |a MOLYBDENUM 
690 1 0 |a THIODISACCHARIDES 
700 1 |a Marino, C. 
700 1 |a Uhrig, M.L. 
700 1 |a Varela, O. 
773 0 |d 2008  |h pp. 540-547  |k n. 3  |p Eur. J. Org. Chem.  |x 1434193X  |w (AR-BaUEN)CENRE-1605  |t European Journal of Organic Chemistry 
856 4 1 |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-38849181001&doi=10.1002%2fejoc.200700874&partnerID=40&md5=021f3f9c7abd8126dbd95c7bf4ec89b4  |y Registro en Scopus 
856 4 0 |u https://doi.org/10.1002/ejoc.200700874  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_1434193X_v_n3_p540_Repetto  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v_n3_p540_Repetto  |y Registro en la Biblioteca Digital 
961 |a paper_1434193X_v_n3_p540_Repetto  |b paper  |c PE 
962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
999 |c 83411 

Ejemplares similares