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:

The use of thiogalactofuranoside as donors for the construction of internal Galf containing oligosaccharide is limited, probably due to the difficulty to functionalize thiogalactofuranoside derivatives showing O-2, O-3, and O-5 with similar reactivity. An efficient method for complete regioselective 5-O-opening of conformationally restricted 3,5-O-di-tert-butylsilylene-d-galactofuranoside derivatives was developed. The use of a solution nBu4NF (1.1 equiv) in CH2Cl2 on 6 gave the 5-OH free derivative 10 as the only product (90%). 3-O-Di-tert-butylhydroxysilyl derivative 10 was stable upon purification and glycosylation reaction. Preactivation of conformationally restricted thioglycoside 6 employing p-NO2-benzensulfenyl chloride/AgOTf followed by condensation over the 5-OH thioglycoside acceptor 10 gave the corresponding disaccharide 12 without autocondensation byproduct. Regioselective 5-O-deprotection was also successfully performed over the (1→5)-β-d-galactofuranosyl di- and trisaccharide derivatives 12 and 13. This methodology allowed the differentiation between the secondary hydroxyl groups OH-3 and OH-5 of 1,2-cis or 1,2-trans d-galactofuranoside derivatives, and it still constitutes an innovative approach to access oligosaccharides of pharmacological importance. © 2016 American Chemical Society.

Registro:

Documento: Artículo
Título:Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene- d -galactofuranosides. Synthesis of (1→5)-β- d -Galactofuranosyl Derivatives
Autor:Tilve, M.J.; Cori, C.R.; Gallo-Rodriguez, C.
Filiación:CIHIDECAR, Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón II, Buenos Aires, 1428, Argentina
Palabras clave:Oligosaccharides; Autocondensation; Glycosylation reactions; Hydroxyl groups; Innovative approaches; Regio-selective; Thioglycosides; Regioselectivity; disaccharide; furan derivative; galactose oligosaccharide; hydroxyl group; n acetylgalactosamine; oligosaccharide; thioglycoside; trisaccharide; acetylation; acylation; alkylation; Article; benzylation; carbohydrate synthesis; conformation; conformational transition; deacylation; glycosylation; ion transport; one pot synthesis; regioselectivity; ring opening; stereochemistry
Año:2016
Volumen:81
Número:20
Página de inicio:9585
Página de fin:9594
DOI: http://dx.doi.org/10.1021/acs.joc.6b01562
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v81_n20_p9585_Tilve

Referencias:

  • (2009) Essentials of Glycobiology, , 2 nd ed. Cold Spring Harbor Laboratory Press: New York
  • Boltje, T.J., Buskas, T., Boons, G.-J., (2009) Nat. Chem., 1, pp. 611-622
  • Wang, L.-X., Davis, B.G., (2013) Chemical Science, 4, pp. 3381-3394
  • Hudak, J.E., Bertozzi, C.R., (2014) Chem. Biol., 21, pp. 16-37
  • Stallforth, P., Lepenies, B., Adibekian, A., Seeberger, P.H., (2009) J. Med. Chem., 52, pp. 5561-5577
  • Peltier, P., Euzen, R., Daniellou, R., Nugier-Chauvin, C., Ferrieres, V., (2008) Carbohydr. Res., 343, pp. 1897-1923
  • Richards, M.R., Lowary, T.L., (2009) ChemBioChem, 10, pp. 1920-1938
  • Marino, C., Gallo-Rodriguez, C., De Lederkremer, R.M., (2012) Glycans: Biochemistry, Characterization and Applications, pp. 207-268. , Mora Montes, H. M. Nova Science: Hauppauge, New York
  • Pedersen, L.L., Turco, S.J., (2003) Cell. Mol. Life Sci., 60, pp. 259-266
  • Eppe, G., El Bkassiny, S., Vincent, S.P., (2015) Carbohydrates in Drug Design and Discovery, pp. 209-241. , The Royal Society of Chemistry: London
  • Chiodo, F., Marradi, M., Park, J., Ram, A.F.J., Penadés, S., Van Die, I., Tefsen, B., (2014) ACS Chem. Biol., 9, pp. 383-389
  • Completo, G.C., Lowary, T.L., (2008) J. Org. Chem., 73, pp. 4513-4525
  • Beláňová, M., Dianišková, P., Brennan, P.J., Completo, G.C., Rose, N.L., Lowary, T.L., Mikušová, K., (2008) J. Bacteriol., 190, pp. 1141-1145
  • Cattiaux, L., Sendid, B., Collot, M., MacHez, E., Poulain, D., Mallet, J.-M., (2011) Bioorg. Med. Chem., 19, pp. 547-555
  • Imamura, A., Lowary, T., (2011) Trends Glycosci. Glycotechnol., 23, pp. 134-152
  • Kashiwagi, G.A., Mendoza, V.M., De Lederkremer, R.M., Gallo-Rodriguez, C., (2012) Org. Biomol. Chem., 10, pp. 6322-6332
  • Mendoza, V.M., Kashiwagi, G.A., De Lederkremer, R.M., Gallo-Rodriguez, C., (2010) Carbohydr. Res., 345, pp. 385-396
  • Krylov, V.B., Argunov, D.A., Vinnitskiy, D.Z., Verkhnyatskaya, S.A., Gerbst, A.G., Ustyuzhanina, N.E., Dmitrenok, A.S., Nifantiev, N.E., (2014) Chem. - Eur. J., 20, pp. 16516-16522
  • Argunov, D.A., Krylov, V.B., Nifantiev, N.E., (2015) Org. Biomol. Chem., 13, pp. 3255-3267
  • Gola, G., Gallo-Rodriguez, C., (2014) RSC Adv., 4, pp. 3368-3382
  • Gandolfi-Donadio, L., Santos, M., De Lederkremer, R.M., Gallo-Rodriguez, C., (2011) Org. Biomol. Chem., 9, pp. 2085-2097
  • Pathak, A.K., Pathak, V., Seitz, L., Maddry, J.A., Gurcha, S.S., Besra, G.S., Suling, W.J., Reynolds, R.C., (2001) Bioorg. Med. Chem., 9, pp. 3129-3143
  • Hanashima, S., Yamaguchi, Y., Ito, Y., (2009) Tetrahedron Lett., 50, pp. 6150-6153
  • Zhu, S.-Y., Yang, J.-S., (2012) Tetrahedron, 68, pp. 3795-3802
  • Deng, L.-M., Liu, X., Liang, X.-Y., Yang, J.-S., (2012) J. Org. Chem., 77, pp. 3025-3037
  • Wang, S., Meng, X., Huang, W., Yang, J.-S., (2014) J. Org. Chem., 79, pp. 10203-10217
  • Gao, P.-C., Zhu, S.-Y., Cao, H., Yang, J.-S., (2016) J. Am. Chem. Soc., 138, pp. 1684-1688
  • Zhu, K., Yang, J.-S., (2016) Tetrahedron, 72, pp. 3113-3123
  • Tilve, M.J., Gallo-Rodriguez, C., (2014) Carbohydr. Res., 397, pp. 7-17
  • Tilve, M.J., Gallo-Rodriguez, C., (2011) Carbohydr. Res., 346, pp. 2838-2848
  • 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
  • Kaeothip, S., Boons, G.-J., (2013) Org. Biomol. Chem., 11, pp. 5136-5146
  • Rao, Y., Boons, G.-J., (2007) Angew. Chem., Int. Ed., 46, pp. 6148-6151
  • Joe, M., Bai, Y., Nacario, R.C., Lowary, T.L., (2007) J. Am. Chem. Soc., 129, pp. 9885-9901
  • Trost, B.M., Caldwell, C.G., (1981) Tetrahedron Lett., 22, pp. 4999-5002
  • Imamura, A., Ando, H., Korogi, S., Tanabe, G., Muraoka, O., Ishida, H., Kiso, M., (2003) Tetrahedron Lett., 44, pp. 6725-6728
  • Imamura, A., Ando, H., Ishida, H., Kiso, M., (2005) Org. Lett., 7, pp. 4415-4418
  • Imamura, A., Kimura, A., Ando, H., Ishida, H., Kiso, M., (2006) Chem. - Eur. J., 12, pp. 8862-8870
  • Heuckendorff, M., Bendix, J., Pedersen, C.M., Bols, M., (2014) Org. Lett., 16, pp. 1116-1119
  • Liang, X.-Y., Bin, H.-C., Yang, J.-S., (2013) Org. Lett., 15, pp. 2834-2837
  • Crouch, D.R., (2004) Tetrahedron, 60, pp. 5833-5871
  • Hsieh, H.-W., Schombs, M.W., Witschi, M.A., Gervay-Hague, J., (2013) J. Org. Chem., 78, pp. 9677-9688
  • Crouch, R.D., (2013) Tetrahedron, 69, pp. 2383-2417
  • Tanino, K., Shimizu, T., Kuwahara, M., Kuwajima, I., (1998) J. Org. Chem., 63, pp. 2422-2423
  • Yu, M., Pagenkopf, B.L., (2002) J. Org. Chem., 67, pp. 4553-4558
  • Furusawa, K., Sakai, T., Tsuda, K., (1988) Jpn. Kokai Tokkyo Koho, p. 913
  • Ohtawa, M., Tomoda, H., Nagamitsu, T., (2014) Bull. Chem. Soc. Jpn., 87, pp. 113-118
  • Chando, K.M., Bailey, P.A., Abramite, J.A., Sammakia, T., (2015) Org. Lett., 17, pp. 5196-5199
  • Gola, G., Liebenson, P., Gandolfi-Donadio, L., Gallo-Rodriguez, C., (2005) Arkivoc, 12, pp. 234-242
  • Gola, G., Tilve, M.J., Gallo-Rodriguez, C., (2011) Carbohydr. Res., 346, pp. 1495-1502
  • Furusawa, K., (1989) Chem. Lett., 18, pp. 509-510
  • Marino, C., Miletti, L., Manso Alves, M.J., Colli, W., De Lederkremer, R.M., (1998) Glycobiology, 8, pp. 901-904
  • Veeneman, G.H., Notermans, S., Liskamp, R.M.J., Van Der Marel, G.A., Van Boom, J.H., (1987) Tetrahedron Lett., 28, pp. 6695-6698
  • Veeneman, G.H., Van Boom, J.H., Notermans, S., Hoogerhout, P., (1989) Recueil des Travaux Chimiques des Pays-Bas, 108, pp. 344-350
  • Veeneman, G.H., Hoogerhout, P., Westerduin, P., Van Boom, J.H., Notermans, S., (1987) Recueil des Travaux Chimiques des Pays-Bas, 106, pp. 129-131
  • Crich, D., Cai, F., Yang, F., (2008) Carbohydr. Res., 343, pp. 1858-1862
  • Peng, P., Geng, Y., Göttker-Schnetmann, I., Schmidt, R.R., (2015) Org. Lett., 17, pp. 1421-1424
  • Peng, P., Liu, H., Gong, J., Nicholls, J.M., Li, X., (2014) Chemical Science, 5, pp. 3634-3639
  • Boltje, T.J., Zhong, W., Park, J., Wolfert, M.A., Chen, W., Boons, G.-J., (2012) J. Am. Chem. Soc., 134, pp. 14255-14262
  • Christina, A.E., Muns, J.A., Olivier, J.Q.A., Visser, L., Hagen, B., Van Den Bos, L.J., Overkleeft, H.S., Van Der Marel, G.A., (2012) Eur. J. Org. Chem., 2012, pp. 5729-5737
  • Veerapen, N., Leadbetter, E.A., Brenner, M.B., Cox, L.R., Besra, G.S., (2010) Bioconjugate Chem., 21, pp. 741-747
  • Matsuo, I., Wada, M., Manabe, S., Yamaguchi, Y., Otake, K., Kato, K., Ito, Y., (2003) J. Am. Chem. Soc., 125, pp. 3402-3403
  • Smith, A.B., Chen, S.S.-Y., Nelson, F.C., Reichert, J.M., Salvatore, B.A., (1995) J. Am. Chem. Soc., 117, pp. 12013-12014

Citas:

---------- APA ----------
Tilve, M.J., Cori, C.R. & Gallo-Rodriguez, C. (2016) . Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene- d -galactofuranosides. Synthesis of (1→5)-β- d -Galactofuranosyl Derivatives. Journal of Organic Chemistry, 81(20), 9585-9594.
http://dx.doi.org/10.1021/acs.joc.6b01562
---------- CHICAGO ----------
Tilve, M.J., Cori, C.R., Gallo-Rodriguez, C. "Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene- d -galactofuranosides. Synthesis of (1→5)-β- d -Galactofuranosyl Derivatives" . Journal of Organic Chemistry 81, no. 20 (2016) : 9585-9594.
http://dx.doi.org/10.1021/acs.joc.6b01562
---------- MLA ----------
Tilve, M.J., Cori, C.R., Gallo-Rodriguez, C. "Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene- d -galactofuranosides. Synthesis of (1→5)-β- d -Galactofuranosyl Derivatives" . Journal of Organic Chemistry, vol. 81, no. 20, 2016, pp. 9585-9594.
http://dx.doi.org/10.1021/acs.joc.6b01562
---------- VANCOUVER ----------
Tilve, M.J., Cori, C.R., Gallo-Rodriguez, C. Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene- d -galactofuranosides. Synthesis of (1→5)-β- d -Galactofuranosyl Derivatives. J. Org. Chem. 2016;81(20):9585-9594.
http://dx.doi.org/10.1021/acs.joc.6b01562