Gemini surfactants from alkyl glucosides

1,5-Bis-[6-O-(n-butyl α-D-glucopyranosid)] glutarate 7 was synthesized starting from D-glucose by a simple procedure. The anomeric mixture of alkylglucosides was separated by flash chromatography of their peracetates. Detritylation in neutral conditions is described. This is the first example of a n...

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Autor principal: Castro, M.J.L
Otros Autores: Kovensky, J., Fernández Cirelli, A.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Elsevier Ltd 1997
Acceso en línea:Registro en Scopus
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Aporte de:Registro referencial: Solicitar el recurso aquí
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100 1 |a Castro, M.J.L. 
245 1 0 |a Gemini surfactants from alkyl glucosides 
260 |b Elsevier Ltd  |c 1997 
270 1 0 |m Cirelli, A.F.; Departamento Quimica Organica, Fac. Ciencias Exactas y Naturales, Universidad Buenos Aires, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
504 |a Menger, F.M., Littau, C.A., (1991) J. Am. Chem. Soc., 113, pp. 1451-1452 
504 |a Karaborni, S., Esselink, K., Hilbers, P.A.J., Smit, B., Karthäuser, J., Van Os, N.M., Zana, R., (1994) Science, 265, pp. 254-256 
504 |a Huo, Q., Leon, R., Petroff, P.M., Stucky, G.D., (1995) Science, 268, pp. 1324-1327 
504 |a Gouéth, P., Ramiz, A., Ronco, G., Mackenzie, G., Villa, P., (1995) Carbohydr. Res., 266, pp. 171-189 
504 |a Schmidt, R.R., Jankowski, K., (1996) Liebigs Ann., pp. 867-879 
504 |a Matsumura, S., Imai, K., Yoshikawa, S., Kawada, K., Uchibori, T., (1990) J. Am. Oil. Chem. Soc., 67, pp. 996-1001 
504 |a AMPAC Version 5.0, , Semichem Inc., 7128 Summit 
504 |a Dewar, M.J.S., Zoebisch, E.F., Healy, E.F., Stewart, J.J.P., (1985) J. Am. Chem. Soc., 107, pp. 3902-3909 
504 |a Lorenz, K., Balzer, W., Wolf, H., Trieselt, W., Busse, G., DE 3,232,791; (1984) C. A., 101, p. 73052 
504 |a Pyridinium chloride (0.75 eq.) in refluxing ethanol was found to be a mild method of detritylation, yielding quantitatively the deprotected product. These neutral conditions may be useful for detritylation of carbohydrate derivatives having acid-sensitive protecting groups and have been successfully tested in our lab on mono- and ditrityl derivatives; Grindley, T.B., Namazi, H., (1996) Tetrahedron Lett., 37, pp. 991-994 
504 |a note; note 
520 3 |a 1,5-Bis-[6-O-(n-butyl α-D-glucopyranosid)] glutarate 7 was synthesized starting from D-glucose by a simple procedure. The anomeric mixture of alkylglucosides was separated by flash chromatography of their peracetates. Detritylation in neutral conditions is described. This is the first example of a non ionic gemini surfactant where alkyl glucosides are linked through a spacer at C-6.  |l eng 
536 |a Detalles de la financiación: Universidad de Buenos Aires 
536 |a Detalles de la financiación: ACKNOWLEDGEMENTS: This work was carried out with the financial contribution of UBA (Universidad de Buenos Aires) and CONICET (Consejo National de Investigaciones Cientificas y Tecnicas). M. Castro thanks Universidad de Buenos Aires for a fellowship. Elemental analyses were performed by UMYMFOR (CONICET). 
593 |a Ctro. Invest. en Hidratos de Carbono, Depto. de Quim. Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
690 1 0 |a GLUTARIC ACID DERIVATIVE 
690 1 0 |a GLYCOSIDE 
690 1 0 |a SURFACTANT 
690 1 0 |a ARTICLE 
690 1 0 |a CHEMICAL REACTION 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a MOLECULAR DYNAMICS 
700 1 |a Kovensky, J. 
700 1 |a Fernández Cirelli, A. 
773 0 |d Elsevier Ltd, 1997  |g v. 38  |h pp. 3995-3998  |k n. 23  |p TETRAHEDRON LETT.  |x 00404039  |w (AR-BaUEN)CENRE-415  |t Tetrahedron Letters 
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856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00404039_v38_n23_p3995_Castro  |y Handle 
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