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Abstract:

A direct synthesis of enantiomerically pure (2S,4S,5R)-4,5,6-trihydroxynorleucine (1) from a carbohydrate precursor (D-glucosamine), is described. D-glucosamine was oxidized to 2-amino-2-deoxy-D-gluconic acid (2), which was converted into the 2-acylamido-hex-2-enono-1,4-(3, 4) and 1,5-lactone (5, 6, 11) derivatives. The hydrogenation of the enamine system of these compounds took place with excellent diastereofacial selectivity leading to the corresponding 3-deoxy-D-arabino-lactone derivatives (7-10, 12, 13). On N-deacetylation with HCl the hydrochloride derivative of 1, in its 1,4-lactone form, was obtained with 57% overall yield, from 2. The ammonium salt of 1 was also prepared. © 1994.

Registro:

Documento: Artículo
Título:A short synthesis of (2S,4S,5R)-4,5,6-trihydroxynorleucine
Autor:Varela, O.; Nin, A.P.; De Lederkremer, R.M.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires. Ciudad Universitaria. Pabellón II, 1428 Buenos Aires, Argentina
Palabras clave:4,5,6 trihydroxynorleucine; hydroxyamino acid; unclassified drug; article; drug synthesis; enantiomer; nuclear magnetic resonance; reaction analysis
Año:1994
Volumen:35
Número:50
Página de inicio:9359
Página de fin:9362
DOI: http://dx.doi.org/10.1016/S0040-4039(00)78542-X
Título revista:Tetrahedron Letters
Título revista abreviado:Tetrahedron Lett.
ISSN:00404039
CODEN:TELEA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v35_n50_p9359_Varela

Referencias:

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  • Drauz, Kleeman, Martens, Induction of Asymmetry by Amino Acids (1982) Angewandte Chemie International Edition in English, 21, pp. 584-608. , Int. Ed. Engl
  • Williams, (1989) Synthesis of Optically Active α-Amino Acids, , Pergamon Press, Oxford
  • Corey, Lee, Choi, An enantioselective synthesis of (2S,3S)- and (2R,3S)-3-hydroxyleucine (1992) Tetrahedron Letters, 33, pp. 6735-6738. , and references therein
  • Cintas, Asymmetric synthesis of α-amino acids from carbohydrates as chiral templates (1991) Tetrahedron, 47, pp. 6079-6111
  • Lederkremer, Varela, Synthetic Reactions of Aldonolactones (1994) Advan. Carbohydr. Chem. Biochem., 50, pp. 125-209
  • Bruce, Fleet, di, Winchester, Iminoheptitols as glycosidase inhibitors: Synthesis of α-homomannojirimycin, 6-epi-α-homomannojirimycin and of a highly substituted pipecolic acid (1992) Tetrahedron, 48, pp. 10191-10200. , and references therein
  • Vekemans, de, Caris, Kokx, Konings, Godefroi, Chittenden, Vitamin C and isovitamin C derived chemistry. 2. Synthesis of some enantiomerically pure 4,5,6-trihydroxylated norleucines (1987) The Journal of Organic Chemistry, 52, pp. 1093-1099
  • Nin, Varela, Lederkremer, Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine. (1993) Tetrahedron, 49, pp. 9459-9464
  • Wolfrom, Cron, Acyl Derivatives of D-Glucosaminic Acid (1952) Journal of the American Chemical Society, 74, pp. 1715-1716
  • Horton, Thomson, Varela, Nin, Lederkremer, Confirmation of the structures of the products obtained on acylation of 2-amino-2-deoxy-d-gluconic acid (1989) Carbohydrate Research, 193, pp. 49-60
  • Marino, Varela, Lederkremer, Benzoylated hexa-2,4-dien-4-olides from aldono-1,4-lactones: Stereoselective synthesis of dideoxyaldonolactone derivatives (1991) Carbohydrate Research, 220, pp. 145-153
  • Moradei, du, Varela, Lederkremer, Synthesis of Furanose Glycosides of Abequose (3, 6-Dideoxy-D-Xylo-Hexose) (1991) Journal of Carbohydrate Chemistry, 10, pp. 469-479
  • Jeroncic, Fernández, Lederkremer, Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose (1987) Carbohydrate Research, 167, pp. 175-186
  • Hussain, Ollis, Smith, Stoddart, The stereochemistry of 2,4- and 2,3-disubstituted-?-butyrolactones (1975) Journal of the Chemical Society, Perkin Transactions 1, pp. 1480-1492
  • All new compounds gave satisfactory elemental analysis. Optical rotations were measured for 1% solutions in CHCl3, unless otherwise indicated; Lederkremer, Litter, Sala, β-Elimination in aldonolactones: a convenient synthesis of 2,4,6-tri-O-benzoyl-3-deoxy-D-arabino-hexono-1,5-lactone (1974) Carbohydrate Research, 36, pp. 185-187
  • Nelson, Factors influencing conformational preference and equilibria in solutions of aldono-1,5-lactones (1987) Carbohydrate Research, 163, pp. 275-278
  • Varela, Fernández, Lederkremer, β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose) (1979) Carbohydrate Research, 70, pp. 27-35

Citas:

---------- APA ----------
Varela, O., Nin, A.P. & De Lederkremer, R.M. (1994) . A short synthesis of (2S,4S,5R)-4,5,6-trihydroxynorleucine. Tetrahedron Letters, 35(50), 9359-9362.
http://dx.doi.org/10.1016/S0040-4039(00)78542-X
---------- CHICAGO ----------
Varela, O., Nin, A.P., De Lederkremer, R.M. "A short synthesis of (2S,4S,5R)-4,5,6-trihydroxynorleucine" . Tetrahedron Letters 35, no. 50 (1994) : 9359-9362.
http://dx.doi.org/10.1016/S0040-4039(00)78542-X
---------- MLA ----------
Varela, O., Nin, A.P., De Lederkremer, R.M. "A short synthesis of (2S,4S,5R)-4,5,6-trihydroxynorleucine" . Tetrahedron Letters, vol. 35, no. 50, 1994, pp. 9359-9362.
http://dx.doi.org/10.1016/S0040-4039(00)78542-X
---------- VANCOUVER ----------
Varela, O., Nin, A.P., De Lederkremer, R.M. A short synthesis of (2S,4S,5R)-4,5,6-trihydroxynorleucine. Tetrahedron Lett. 1994;35(50):9359-9362.
http://dx.doi.org/10.1016/S0040-4039(00)78542-X