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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| Lenguaje: | Inglés |
| Publicado: |
1994
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 06088caa a22006377a 4500 | ||
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| 001 | PAPER-1 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518202923.0 | ||
| 008 | 190411s1994 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0027941639 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a TELEA | ||
| 100 | 1 | |a Varela, O. | |
| 245 | 1 | 2 | |a A short synthesis of (2S,4S,5R)-4,5,6-trihydroxynorleucine |
| 260 | |c 1994 | ||
| 270 | 1 | 0 | |m Varela, O.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires. Ciudad Universitaria. Pabellón II, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Wagner, Musso, New Naturally Occurring Amino Acids (1983) Angewandte Chemie International Edition in English, 22, pp. 816-828. , Int. Ed. Engl | ||
| 504 | |a Drauz, Kleeman, Martens, Induction of Asymmetry by Amino Acids (1982) Angewandte Chemie International Edition in English, 21, pp. 584-608. , Int. Ed. Engl | ||
| 504 | |a Williams, (1989) Synthesis of Optically Active α-Amino Acids, , Pergamon Press, Oxford | ||
| 504 | |a Corey, Lee, Choi, An enantioselective synthesis of (2S,3S)- and (2R,3S)-3-hydroxyleucine (1992) Tetrahedron Letters, 33, pp. 6735-6738. , and references therein | ||
| 504 | |a Cintas, Asymmetric synthesis of α-amino acids from carbohydrates as chiral templates (1991) Tetrahedron, 47, pp. 6079-6111 | ||
| 504 | |a Lederkremer, Varela, Synthetic Reactions of Aldonolactones (1994) Advan. Carbohydr. Chem. Biochem., 50, pp. 125-209 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a Nin, Varela, Lederkremer, Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine. (1993) Tetrahedron, 49, pp. 9459-9464 | ||
| 504 | |a Wolfrom, Cron, Acyl Derivatives of D-Glucosaminic Acid (1952) Journal of the American Chemical Society, 74, pp. 1715-1716 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a Jeroncic, Fernández, Lederkremer, Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose (1987) Carbohydrate Research, 167, pp. 175-186 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a Nelson, Factors influencing conformational preference and equilibria in solutions of aldono-1,5-lactones (1987) Carbohydrate Research, 163, pp. 275-278 | ||
| 504 | |a Varela, Fernández, Lederkremer, β-Elimination in aldonolactones. Synthesis of 3,6-dideoxy L-arabino-hexose (ascarylose) (1979) Carbohydrate Research, 70, pp. 27-35 | ||
| 520 | 3 | |a 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. |l eng | |
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires. Ciudad Universitaria. Pabellón II, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 4,5,6 TRIHYDROXYNORLEUCINE |
| 690 | 1 | 0 | |a HYDROXYAMINO ACID |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a ENANTIOMER |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE |
| 690 | 1 | 0 | |a REACTION ANALYSIS |
| 700 | 1 | |a Nin, A.P. | |
| 700 | 1 | |a De Lederkremer, R.M. | |
| 773 | 0 | |d 1994 |g v. 35 |h pp. 9359-9362 |k n. 50 |p Tetrahedron Lett. |x 00404039 |w (AR-BaUEN)CENRE-415 |t Tetrahedron Letters | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/S0040-4039(00)78542-X |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00404039_v35_n50_p9359_Varela |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v35_n50_p9359_Varela |y Registro en la Biblioteca Digital |
| 961 | |a paper_00404039_v35_n50_p9359_Varela |b paper |c PE | ||
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| 963 | |a VARI | ||
| 999 | |c 60954 | ||