Navegar

Colección

Datos Estadísticas

Artículo

El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Conformationally restricted 3,5-O-di-tert-butylsilylene-d-galactofuranosyl trichloroacetimidate donors were synthesized from allyl α-d- galactofuranoside for the construction of 1,2-cis α-d-galactofuranosyl linkages. Glycosylation reactions were performed with several acceptors, including d-galactono-1,4-lactone, d-rhamnopyranosyl, and d-mannopyranosyl derivatives. The influence of the temperature and the reaction solvents was evaluated, as well as the 6-O-substitution pattern of the donor. The higher α-selectivities were obtained at -78 °C in diethyl ether as solvent. 6-O-Acetyl substitution on constrained donor increased the α-selectivity compared to the 6-O-benzyl substitution. Almost no selectivities were observed in the non-participating solvent CH 2Cl 2. In contrast, ethereal solvents enhanced the α-selectivity suggesting a participating effect in the reaction intermediate. © 2011 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation
Autor:Tilve, M.J.; Gallo-Rodriguez, C.
Filiación:CIHIDECAR, Departamento de Química Orgánica, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Palabras clave:1,2-cis; Galactofuranose; Glycosylation; Protecting groups; Solvents effects; Trichloroacetimidate; 1,2-cis; Diethyl ethers; Ethereal solvents; Galactofuranose; Glycosylation reactions; Protecting groups; Reaction solvents; Trichloroacetimidate; Esterification; Ethers; Glycosylation; Reaction intermediates; Solvents; 3,5 o (di tert butylsilylene) dextro galactofuranosyl trichloroacetimidate; dextro galactono 1,4 lactone; dichloromethane; glucose derivative; lactone derivative; trichloroacetimidic acid; unclassified drug; article; conformation; glycosylation; priority journal; reaction analysis; synthesis; temperature; Carbohydrate Conformation; Furans; Galactosides; Glycosylation; Organosilicon Compounds
Año:2011
Volumen:346
Número:18
Página de inicio:2838
Página de fin:2848
DOI: http://dx.doi.org/10.1016/j.carres.2011.10.004
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:dichloromethane, 75-09-2; Furans; Galactosides; Organosilicon Compounds
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n18_p2838_Tilve

Referencias:

  • Boltje, T.J., Buskas, T., Boons, G.-J., (2009) Nat. Chem., 1, pp. 611-622
  • Stallforth, P., Lepenies, B., Adibekian, A., Seeberger, P.H., (2009) J. Med. Chem., 52, pp. 5561-5577
  • Varki, A., Cummings, R.D., Esko, J.D., Freeze, H.H., Stanley, P., Bertozzi, C.R., Hart, G.W., Etzler, M.E., (2009) Essentials of Glycobiology, , 2nd ed. Cold Spring Harbor Laboratory Press New York
  • Zhu, X., Schmidt, R.R., (2009) Angew. Chem., Int. Ed., 48, pp. 1900-1934
  • Demchenko, A.V., (2003) Curr. Org. Chem., 7, pp. 35-79
  • Peltier, P., Euzen, R., Daniellou, R., Nugier-Chauvin, C., Ferrires, V., (2008) Carbohydr. Res., 343, pp. 1897-1923
  • Richards, M.R., Lowary, T.L., (2009) ChemBioChem, 10, pp. 1920-1938
  • Lowary, T.L., (2003) Curr. Opin. Chem. Biol., 7, pp. 749-756
  • Houseknecht, J.B., Lowary, T.L., (2001) Curr. Opin. Chem. Biol., 5, pp. 677-682
  • Imamura, A., Lowary, T.L., (2011) Trends Glycosci. Glycotechnol., 23, pp. 134-152
  • Lederkremer, R.M., Colli, W., (1995) Glycobiology, 5, pp. 547-552
  • Pedersen, L.L., Turco, S.J., (2003) Cell. Mol. Life Sci., 60, pp. 259-266
  • Tam, P.-H., Lowary, T.L., (2009) Curr. Opin. Chem. Biol., 13, pp. 618-625
  • Belanova, M., Dianiskova, P., Brennan, P.J., Completo, G.C., Rose, N.L., Lowary, T.L., Mikusova, K., (2008) J. Bacteriol., 190, pp. 1141-1145
  • Richards, J.C., Perry, M.B., Kniskern, P.J., (1989) Can. J. Chem., 67, pp. 1038-1050
  • Linnerborg, M., Wollin, R., Wildmalm, G., (1997) Eur. J. Biochem., 246, pp. 565-573
  • Perepelov, A.V., Li, D., Liu, B., Senchenkova, S.N., Guo, D., Shashkov, A.S., Feng, L., Wang, L., (2011) Innate Immun., 17, pp. 164-173
  • Perepelov, A.V., Liu, B., Senchenkova, S.N., Shashkov, A.S., Feng, L., Knirel, Y.A., Wang, L., (2011) Carbohydr. Res., 346, pp. 373-376
  • Ahrazem, O., Prieto, A., San-Blas, G., Leal, J.A., Jimenez-Barbero, J., Bernabé, M., (2003) Glycobiology, 13, pp. 743-747
  • Gelin, M., Ferrires, V., Plusquellec, D., (1997) Carbohydr. Lett., 2, pp. 381-388
  • Gandolfi-Donadio, L., Gola, G., De Lederkremer, R.M., Gallo-Rodriguez, C., (2006) Carbohydr. Res., 341, pp. 2487-2497
  • Ghosh, S., Misra, A.K., (2010) Tetrahedron: Asymmetry, 21, pp. 2755-2761
  • Gola, G., Tilve, M.J., Gallo-Rodriguez, C., (2011) Carbohydr. Res., 346, pp. 1495-1502
  • Guelin, M., Ferrieres, V., Plusquellec, D., (2000) Eur. J. Org. Chem., pp. 1423-1431
  • Lee, Y.J., Lee, B.-Y., Jeon, H.B., Kim, K.S., (2006) Org. Lett., 8, pp. 3971-3974
  • Baek, J.Y., Joo, Y.J., Kim, K.S., (2008) Tetrahedron Lett., 49, pp. 4734-4737
  • Bai, Y., Lowary, T.L., (2006) J. Org. Chem., 71, pp. 9658-9671
  • Bai, Y., Lowary, T.L., (2006) J. Org. Chem., 71, pp. 9672-9680
  • Mydock, L.K., Demchenko, A.V., (2010) Org. Biomol. Chem., 8, pp. 497-510
  • Bohé, L., Crich, D., (2011) C.R. Chim., 14, pp. 3-16
  • Crich, D., (2010) Acc. Chem. Res., 43, pp. 1144-1153
  • Manabe, S., Ito, Y., (2008) Curr. Bioact. Compd., 4, pp. 258-281
  • Walvoort, M.T.C., Dinkelaar, J., Van Den Bos, L.J., Lodder, G., Overkleeft, H.S., Codée, J.D.C., Van Der Marel, G.A., (2010) Carbohydr. Res., 345, pp. 1252-1263
  • Guo, J., Ye, X.-S., (2010) Molecules, 15, pp. 7235-7265
  • Smith, D.M., Tran, M.B., Woerpel, K.A., (2003) J. Am. Chem. Soc., 125, pp. 14149-14152
  • Larsen, C.H., Ridgway, B.H., Shaw, J.T., Smith, D.M., Woerpel, K.A., (2005) J. Am. Chem. Soc., 127, pp. 10879-10884
  • Zhu, X., Kawatkar, S., Rao, Y., Boons, G.-J., (2006) J. Am. Chem. Soc., 128, pp. 11948-11957
  • Crich, D., Pedersen, C.M., Bowers, A.A., Wink, D.J., (2007) J. Org. Chem., 72, pp. 1553-1565
  • Wang, Y., Maguire-Boyle, S., Dere, R.T., Zhu, X., (2008) Carbohydr. Res., 343, pp. 3100-3106
  • Nacario, R.C., Lowary, T.L., McDonald, R., (2007) Acta Crystallogr., Sect. e, 63, pp. 498-o500
  • Joe, M., Bai, Y., Nacario, R.C., Lowary, T.L., (2007) J. Am. Chem. Soc., 129, pp. 9885-9901
  • Rademacher, C., Shoemaker, G.K., Kim, H.-S., Zheng, R.B., Taha, H., Liu, C., Nacario, R.C., Lowary, T.L., (2007) J. Am. Chem. Soc., 129, pp. 10489-10502
  • Rao, Y., Boons, G.-J., (2007) Angew. Chem., Int. Ed., 46, pp. 6148-6151
  • Rao, Y., Buskas, T., Albert, A., O'Neill, M.A., Hahn, M.G., Boons, G.-J., (2008) ChemBioChem, 9, pp. 381-388
  • Ishiwata, A., Akao, H., Ito, Y., (2006) Org. Lett., 8, pp. 5525-5528
  • Ishiwata, A., Ito, Y., (2009) Trends Glycosci. Glycotechnol., 21, pp. 266-289
  • Ishiwata, A., Ito, Y., (2011) J. Am. Chem. Soc., 133, pp. 2275-2291
  • Imamura, A., Lowary, T.L., (2010) Org. Lett., 12, pp. 3686-3689
  • Schmidt, R.R., Zhu, X., Glycosyl Trichloroacetimidates (2008) Glycoscience, pp. 451-453. , B. Fraser-Reid, K. Tatsuta, J. Thiem, Springer-Verlag Berlin Heidelberg
  • Schmidt, R.R., Kinzy, W., (1994) Adv. Carbohydr. Chem. Biochem., 50, pp. 21-123
  • Gallo-Rodríguez, C., Gandolfi-Donadio, L., De Lederkremer, R.M., (1999) Org. Lett., 1, pp. 245-248
  • Gandolfi-Donadío, L., Gallo-Rodriguez, C., Lederkremer, R.M., (2002) J. Org. Chem., 67, pp. 4430-4435
  • Gandolfi-Donadío, L., Gallo-Rodriguez, C., De Lederkremer, R.M., (2003) J. Org. Chem., 68, pp. 6928-6934
  • Gallo-Rodriguez, C., Gil-Libarona, M.A., Mendoza, V.M., Lederkremer, R.M., (2002) Tetrahedon, 58, pp. 9373-9380
  • Mendoza, V.M., Kashiwagi, G.A., De Lederkremer, R.M., Gallo-Rodriguez, C., (2010) Carbohydr. Res., 345, pp. 385-396
  • Gandolfi-Donadío, L., Santos, M., De Lederkremer, R.M., Gallo-Rodriguez, C., (2011) Org. Biomol. Chem., 9, pp. 2085-2097
  • Qiao, Y., Lindner, B., Zähringer, U., Truog, P., Schmidt, R.R., (2010) Bioorg. Med. Chem., 18, pp. 3696-3702
  • Splain, R.A., Kiessling, L.L., (2010) Bioorg. Med. Chem., 18, pp. 3753-3759
  • Klotz, W., Schmidt, R.R., (1993) Liebigs Ann. Chem., pp. 683-690
  • Gola, G., Libenson, P., Gandolfi-Donadío, L., Gallo-Rodriguez, C., (2005) Arkivoc, 12, pp. 234-242
  • Gelin, M., Ferrieres, V., Lefeuvre, M., Plusquellec, D., (2003) Eur. J. Org. Chem., pp. 1285-1293
  • Jensen, H.S., Limberg, G., Pedersen, C., (1997) Carbohydr. Res., 302, pp. 109-112
  • Eckenberg, P., Groth, U., Huhn, T., Richter, N., Schmeck, C., (1993) Tetrahedron, 49, pp. 1619-1624
  • Wang, P., Haldar, P., Wang, Y., Hu, H., (2007) J. Org. Chem., 72, pp. 5870-5873
  • Sadozai, K.K., Nukada, T., Ito, Y., Nakahara, Y., Ogawa, T., Kobata, A., (1986) Carbohydr. Res., 157, pp. 101-123
  • Kinzy, W., Schmidt, R.R., (1987) Liebigs Ann. Chem., pp. 407-415
  • Kobayashi, M., Yamazaki, F., Ito, Y., Ogawa, T., (1990) Carbohydr. Res., 201, pp. 51-67
  • Lohman, G.J.S., Seeberger, P.H., (2004) J. Org. Chem., 69, pp. 4081-4093
  • Du Mortier, C., Varela, O., De Lederkremer, R.M., (1989) Carbohydr. Res., 189, pp. 79-86
  • Westerduin, P., De Haan, P.E., Deers, M.J., Van Boom, J.H., (1988) Carbohydr. Res., 180, pp. 195-205
  • Baek, J.Y., Lee, B.-Y., Jo, M.G., Kim, K.S., (2009) J. Am. Chem. Soc., 131, pp. 17705-17713
  • Ziegler, T., Kovac, P., Glaudemans, C.P.J., (1989) Carbohydr. Res., 194, pp. 185-198
  • Xie, N., Taylor, C.M., (2010) Org. Lett., 12, pp. 4968-4971

Citas:

---------- APA ----------
Tilve, M.J. & Gallo-Rodriguez, C. (2011) . Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation. Carbohydrate Research, 346(18), 2838-2848.
http://dx.doi.org/10.1016/j.carres.2011.10.004
---------- CHICAGO ----------
Tilve, M.J., Gallo-Rodriguez, C. "Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation" . Carbohydrate Research 346, no. 18 (2011) : 2838-2848.
http://dx.doi.org/10.1016/j.carres.2011.10.004
---------- MLA ----------
Tilve, M.J., Gallo-Rodriguez, C. "Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation" . Carbohydrate Research, vol. 346, no. 18, 2011, pp. 2838-2848.
http://dx.doi.org/10.1016/j.carres.2011.10.004
---------- VANCOUVER ----------
Tilve, M.J., Gallo-Rodriguez, C. Glycosylation studies on conformationally restricted 3,5-O-(di-tert- butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation. Carbohydr. Res. 2011;346(18):2838-2848.
http://dx.doi.org/10.1016/j.carres.2011.10.004