A short synthesis of (2S,4S,5R)-4,5,6-trihydroxynorleucine
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,...
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| Otros Autores: | , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
1994
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| Sumario: | 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. |
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| Bibliografía: | Wagner, Musso, New Naturally Occurring Amino Acids (1983) Angewandte Chemie International Edition in English, 22, pp. 816-828. , Int. Ed. Engl 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 |
| ISSN: | 00404039 |
| DOI: | 10.1016/S0040-4039(00)78542-X |