Michael addition of thiols to sugar enones. Synthesis of 3-deoxy-4-thiohexopyranosid-2-uloses as key precursors of 3-deoxy- and C-2 branched-chain 4-thiosugars

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Benzyl and 2-propyl 6-O-acetyl-3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-uloses (2) and (3) were readily prepared by the tin(IV) chloride-promoted glycosylation of glycal (1). The enone system of (2) and (3) underwent a highly diastereoselective Michael addition of thiols (ethanethiol, propane-2-...

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Detalles Bibliográficos
Autor principal: Uhrig, M.L
Otros Autores: Varela, O.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2002
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Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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030 |a AJCHA 
100 1 |a Uhrig, M.L. 
245 1 0 |a Michael addition of thiols to sugar enones. Synthesis of 3-deoxy-4-thiohexopyranosid-2-uloses as key precursors of 3-deoxy- and C-2 branched-chain 4-thiosugars 
260 |c 2002 
270 1 0 |m Varela, O.; Departamento de Quimica Organica, Universidad de Buenos Aires, Pabellon II, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: varela@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Lichtenthaler, F.W., (1989) Natural Product Chemistry, p. 227. , Ed. Atta-ur-Rahman (Springer: Heidelberg) 
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504 |a Witczak, Z.J., Chhabra, R., Chojnacki, J., (1997) Tetrahedron Lett., 38, p. 2215 
504 |a Shafizadeh, F., Fourneaux, R.H., Stevenson, T.T., (1979) Carbohydr. Res., 71, p. 169 
504 |a Shafizadeh, F., Ward, D.D., Pang, D., (1982) Carbohydr. Res., 102, p. 217 
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504 |a Gómez, M., Quincoces, J., Peseke, K., Michalik, M., Reinke, H., (1999) J. Carbohydr. Chem., 18, p. 851 
504 |a Witczak, Z.J., Chhabra, R., Chen, H., Xie, X.-Q., (1997) Carbohydr. Res., 301, p. 167 
504 |a Kroutil, J., Cerný, M., Trnka, T., Budesínsky, M., (2001) Carbohydr. Res., 334, p. 153 
504 |a De Fina, G., Varela, O., De Lederkremer, R.M., (1988) Synthesis, p. 891 
504 |a Varela, O., De Fina, G., De Lederkremer, R.M., (1987) Carbohydr. Res., 165, p. 187 
504 |a Varela, O., De Fina, G., De Lederkremer, R.M., (1990) J. Chem. Res., Synop., p. 262 
504 |a Varela, O., De Fina, G., De Lederkremer, R.M., (1993) Carbohydr Res., 246, p. 371 
504 |a Di Nardo, C., Varela, O., De Lederkremer, R.M., Baggio, R., Vega, D., Garland, M.T., (1995) Carbohydr. Res., 269, p. 99 
504 |a Zunszain, P.A., Varela, O., (1998) Tetrahedron: Asymmetry, 9, p. 1269 
504 |a Iriarte Capaccio, C., Varela, O., (2000) Tetrahedron: Asymmetry, 11, p. 4945 
504 |a Garbisch, E.W., (1964) J. Am. Chem. Soc., 86, p. 5561 
504 |a Dauben, W.G., Kowalczyk, B.A., Lichtenthaler, F.W., (1990) J. Org. Chem., 55, p. 2391 
504 |a Breitmaier, E., Voelter, W., (1987) Carbon-13 NMR Spectroscopy, 3rd Edition, p. 281. , VCH: Weinheim, Germany 
504 |a Doddrell, D.M., Pegg, D.T., Bendall, M.R., (1982) J. Magn. Res., 48, p. 323 
504 |a (1982) J. Chem. Phys., 77, p. 2745 
504 |a Bock, K., Pederson, C., (1983) Adv. Carbohydr Chem. Biochem., 41, p. 27 
504 |a Lichtenthaler, F.W., Nishiyama, S., Köhler, P., Linder, H.J., (1985) Carbohydr. Res., 136, p. 13 
504 |a Prout, F.S., Beaucaire, V.D., Dyrkacz, G.P., Koppes, W.M., Kuznicki, R.E., Marlewski, T.A., Pienkowski, J.J., Puda, J.M., (1973) J. Org. Chem., 38, p. 1512 
520 3 |a Benzyl and 2-propyl 6-O-acetyl-3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-uloses (2) and (3) were readily prepared by the tin(IV) chloride-promoted glycosylation of glycal (1). The enone system of (2) and (3) underwent a highly diastereoselective Michael addition of thiols (ethanethiol, propane-2-thiol, and benzenemethanethiol) to afford the sulfur-containing hexopyranosid-2-ulose derivatives (4a-c) and (5a-c) in good yields. Sodium borohydride reduction of the carbonyl functionalities of (4b,c) and (5b) led to the corresponding 3-deoxy-4-thiohexopyranosides having the D-xylo (6b), (6c), and (8b) or the D-lyxo (7b), (7c), and (8c) configuration. Standard acetylation of these compounds gave the corresponding per-O-acetyl derivatives (10b), (10c), and (12b) and (11b), (11c), and (13b), useful for confirming all the previous configurational assignments by means of their 1H and 13C nuclear magnetic resonance spectra. Furthermore the 2-ulose (5b) proved to be a key intermediate for the synthesis of C-2 branched-chain 4-thiopyranosides, such as (16). The latter was synthesized by a good yielding ammonium acetate-catalysed Knoevenagel-type condensation of malononitrile with (5b).  |l eng 
593 |a Departamento de Quimica Organica, Universidad de Buenos Aires, Pabellon II, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
690 1 0 |a ACETYLATION 
690 1 0 |a BENZENE 
690 1 0 |a DERIVATIVES 
690 1 0 |a HYDROGEN 
690 1 0 |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY 
690 1 0 |a SYNTHESIS (CHEMICAL) 
690 1 0 |a GLYCOSYLATION 
690 1 0 |a SUGAR ENONES 
690 1 0 |a SUGAR (SUCROSE) 
650 1 7 |2 spines  |a CARBON 
700 1 |a Varela, O. 
773 0 |d 2002  |g v. 55  |h pp. 155-160  |k n. 1-2  |p Aust. J. Chem.  |x 00049425  |w (AR-BaUEN)CENRE-34  |t Australian Journal of Chemistry 
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856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00049425_v55_n1-2_p155_Uhrig  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00049425_v55_n1-2_p155_Uhrig  |y Registro en la Biblioteca Digital 
961 |a paper_00049425_v55_n1-2_p155_Uhrig  |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 66246 

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