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Abstract:

Approaches to the enantioselective synthesis of the useful building blocks (2R)- and (2S)-2-benzyloxy-2(H)-pyran-3(6H)-one (12 and 17, respectively) are described. The most direct and highly yielding route for the synthesis of 12 was based on the 'one-pot' preparation of benzyl 2-O-acetyl-arabinopyranoside 3,4-thionocarbonates (7 and 14) from benzyl β-L- or β-D- arabinopyranosides (1 and 13). Trimethylphosphite-promoted olefination, followed by O-deacetylation and oxidation gave the optically pure enantiomeric enones 12 and 17 in about 50% overall yield. © Georg Thieme Verlag Stuttgart.

Registro:

Documento: Artículo
Título:Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose
Autor:Uhrig, M.L.; Varela, O.
Filiación:CIHIDECAR-CONICET, Depto. de Quím. Orgán., Ciudad Universitaria, 1428, Buenos Aires, Argentina
Palabras clave:Carbohydrates; Chiral pool; Enones; Olefination; Stereoselective synthesis; Acetylation; Benzene; Carbonates; Complexation; Olefins; Oxidation; Deacetylation; Enantiomers; Enantiospecific synthesis; Olefination; Synthesis (chemical); 2 pyrone derivative; arabinose; article; chemical reaction; chemical structure; chirality; deacetylation; enantiomer; enantioselectivity; olefination; oxidation kinetics; reaction analysis; stereochemistry; structure analysis; synthesis
Año:2005
Número:6
Página de inicio:893
Página de fin:898
DOI: http://dx.doi.org/10.1055/s-2005-861833
Título revista:Synthesis
Título revista abreviado:Synthesis
ISSN:00397881
CODEN:SYNTB
CAS:arabinose, 147-81-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n6_p893_Uhrig

Referencias:

  • Ferrier, R.J., Hoberg, J.O., (2003) Adv. Carbohydr. Chem. Biochem., 58, p. 55
  • Lichtenthaler, F.W., (2002) Acc. Chem. Res., 35, p. 728
  • Fraser-Reid, B., (1996) Acc. Chem. Res., 29, p. 57
  • Lichtenthaler, F.W., (1986) Natural Product Synthesis, p. 227. , Atta-ur-Rahman, Ed.; Springer: New York
  • Trost, B.M., King, S.A., Schmidt, T., (1989) J. Am. Chem. Soc., 111, p. 5902
  • Becker, B., (2000) J. Carbohydr. Chem., 19, p. 253
  • Witczak, Z.J., Chhabra, R., Chojnacki, J., (1997) Tetrahedron Lett., 38, p. 2215
  • Witczak, Z.J., Chhabra, R., Chen, H., Xie, X.Q., (1997) Carbohydr. Res., 301, p. 167
  • Horton, D., Roski, J.P., Norris, P., (1996) J. Org. Chem., 61, p. 3783
  • Blake, A.J., Cook, T.A., Forsyth, A.C., Gould, R.O., Paton, R.M., (1992) Tetrahedron, 48, p. 8053
  • Dauben, W.G., Kowalczyk, B.A., Lichtenthaler, F.W., (1990) J. Org. Chem., 55, p. 2391
  • Holder, N.L., (1982) Chem. Rev., p. 287
  • De Fina, G.M., Varela, O., Lederkremer, R.M., (1988) Synthesis, p. 891
  • Iriarte Cappácio, C.A., Varela, O., (2001) J. Org. Chem., 66, p. 8859
  • Iriarte Cappácio, C.A., Varela, O., (2002) J. Org. Chem., 67, p. 7839
  • Iriarte Cappácio, C.A., Varela, O., (2003) Tetrahedron Lett., 44, p. 4023
  • Uhrig, M.L., Varela, O., (2002) Carbohydr. Res., 337, p. 2069
  • Reist, E.J., Gueffroy, D.E., Goodman, L., (1965) J. Am. Chem. Soc., 87, p. 677
  • Haines, A.H., (1976) Adv. Carbohydr. Chem. Biochem., 33, p. 11
  • Horton, D., Thomson, J.K., Tindall Jr., C.G., (1972) Methods Carbohydr. Chem., 6, p. 297
  • Tipson, R.S., Cohen, A., (1965) Carbohydr. Res., 1, p. 338
  • Block, E., (1984) Org. React., 30, p. 457
  • Koll, P., Deyhim, S., (1978) Chem. Ber., 111, p. 2913
  • Procter, G., (1991) Comprehensive Organic Synthesis, 7, p. 305. , Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford
  • Fraser-Reid, B., Walker, D.L., Tam, S.Y.-K., Holder, N.L., (1973) Can. J. Chem., 51, p. 3850
  • Varela, O., (2003) Adv. Carbohydr. Chem. Biochem., 58, p. 307
  • Ley, S.V., Madin, A., (1991) Comprehensive Organic Synthesis, 7, p. 251. , Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford
  • Fletcher Jr., H.G., (1963) Methods Carbohydr. Chem., 2, p. 386
  • McCreary, M.D., Lewis, D.W., Wernick, D.L., Whitesides, G.M., (1974) J. Am. Chem. Soc., 96, p. 1038
  • Mayo, B.C., (1973) Chem. Soc. Rev., p. 249
  • Lichtenthaler, F.W., (1998) Carbohydr. Res., 313, p. 69
  • Giffhorn, F., Köpper, S., Huwig, A., Freimund, S., (2000) Enzyme Microb. Technol., 27, p. 734
  • Attenburrow, J., Cameron, A.F.B., Chapman, J.H., Evans, R.M., Hems, B.A., Jansen, A.B.A., Walker, T., (1952) J. Chem. Soc., p. 1094

Citas:

---------- APA ----------
Uhrig, M.L. & Varela, O. (2005) . Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose. Synthesis(6), 893-898.
http://dx.doi.org/10.1055/s-2005-861833
---------- CHICAGO ----------
Uhrig, M.L., Varela, O. "Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose" . Synthesis, no. 6 (2005) : 893-898.
http://dx.doi.org/10.1055/s-2005-861833
---------- MLA ----------
Uhrig, M.L., Varela, O. "Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose" . Synthesis, no. 6, 2005, pp. 893-898.
http://dx.doi.org/10.1055/s-2005-861833
---------- VANCOUVER ----------
Uhrig, M.L., Varela, O. Enantiospecific synthesis of both enantiomers of 2-benzyloxydihydropyran-3- ones from arabinose. Synthesis. 2005(6):893-898.
http://dx.doi.org/10.1055/s-2005-861833