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Abstract:

Benzoylation of D-glycero-L-manno-heptono-1,4-lactone (1) with benzoyl chloride and pyridine for 2 h afforded crystalline penta-O-benzoyl-D-glycero-L-manno-heptono-1,4-lactone (2), but a large excess of reagent during 8 h also led to 2,5,6,7-tetra-O- benzoyl-3-deoxy-D-lyxo-hept-2-enono-1,4-lactone (3). Catalytic hydrogenation of 3 was stereoselective and gave 2,5,6,7-tetra-O-benzoyl-3-deoxy-D-galacto-heptono-1,4-lactone (4). Debenzoylation of 4 followed by oxidative decarboxylation with ceric sulfate in aqueous sulfuric acid gave 2-deoxy-D-lyxo-hexose (5). Application of the same reaction to 3-deoxy-D-gluco-heptono-1,4-lactone afforded 2-deoxy-D-arabino-hexose (6). © 1980.

Registro:

Documento: Artículo
Título:β-elimination in aldonolactones. Synthesis of 2-deoxy-D-lyxo-hexose and 2-deoxy-D-arabino-hexose
Autor:Sala, L.F.; Fernández Cirelli, A.; de Lederkremer, R.M.
Filiación:Departamento de Quimica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Año:1980
Volumen:78
Número:1
Página de inicio:61
Página de fin:66
DOI: http://dx.doi.org/10.1016/S0008-6215(00)83660-5
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v78_n1_p61_Sala

Referencias:

  • de Lederkremer, Litter, (1971) Carbohydr. Res., 20, pp. 442-444
  • Litter, de Lederkremer, (1973) Carbohydr. Res., 26, pp. 431-434
  • de Lederkremer, Litter, Sala, (1974) Carbohydr. Res., 36, pp. 185-187
  • Varela, Fernández Cirelli, de Lederkremer, (1979) Carbohydr. Res., 70, pp. 27-35
  • de Lederkremer, Sala, (1975) Carbohydr. Res., 40, pp. 385-386
  • Sala, Fernández Cirelli, de Lederkremer, Oxidative decarboxylation of aldonolactones by cerium(IV) sulphate in aqueous sulphuric acid; synthesis of D-arabinose (1977) Journal of the Chemical Society, Perkin Transactions 2, pp. 685-688
  • Sala, Fernández Cirelli, de Lederkremer, (1978) Anal. Asoc. Quim. Argentina, 66, pp. 57-63
  • Litter, de Lederkremer, (1974) Anal. Asoc. Quim. Argentina, 62, pp. 147-150
  • Hudson, (1918) J. Am. Chem. Soc., 40, pp. 813-817
  • Trevelyan, Procter, Harrison, (1950) Nature, 166, pp. 444-445
  • Hough, Jones, Wadman, 345. Quantitative analysis of mixtures of sugars by the method of partition chromatography. Part V. Improved methods for the separation and detection of the sugars and their methylated derivatives on the paper chromatogram (1950) Journal of the Chemical Society (Resumed), pp. 1702-1706
  • Abdel-Akher, Smith, (1951) J. Am. Chem. Soc., 73, pp. 5859-5860
  • Overend, Shafizadeh, Stacey, 131. Deoxy-sugars. Part IX. Some properties and reactions of 2-deoxy-D-galactose (1950) Journal of the Chemical Society (Resumed), pp. 671-677
  • Bolliger, Schmidt, Zur Synthese von 2-Desoxy-D-glucose aus Thio�thern. Thio�ther II (1951) Helvetica Chimica Acta, 34, pp. 1671-1675

Citas:

---------- APA ----------
Sala, L.F., Fernández Cirelli, A. & de Lederkremer, R.M. (1980) . β-elimination in aldonolactones. Synthesis of 2-deoxy-D-lyxo-hexose and 2-deoxy-D-arabino-hexose. Carbohydrate Research, 78(1), 61-66.
http://dx.doi.org/10.1016/S0008-6215(00)83660-5
---------- CHICAGO ----------
Sala, L.F., Fernández Cirelli, A., de Lederkremer, R.M. "β-elimination in aldonolactones. Synthesis of 2-deoxy-D-lyxo-hexose and 2-deoxy-D-arabino-hexose" . Carbohydrate Research 78, no. 1 (1980) : 61-66.
http://dx.doi.org/10.1016/S0008-6215(00)83660-5
---------- MLA ----------
Sala, L.F., Fernández Cirelli, A., de Lederkremer, R.M. "β-elimination in aldonolactones. Synthesis of 2-deoxy-D-lyxo-hexose and 2-deoxy-D-arabino-hexose" . Carbohydrate Research, vol. 78, no. 1, 1980, pp. 61-66.
http://dx.doi.org/10.1016/S0008-6215(00)83660-5
---------- VANCOUVER ----------
Sala, L.F., Fernández Cirelli, A., de Lederkremer, R.M. β-elimination in aldonolactones. Synthesis of 2-deoxy-D-lyxo-hexose and 2-deoxy-D-arabino-hexose. Carbohydr. Res. 1980;78(1):61-66.
http://dx.doi.org/10.1016/S0008-6215(00)83660-5