Artículo
Abstract:
2-Acetamido-4,6-O-benzylidene-2,3-dideoxy-D-erythro-hex-2-enono-1,5-la ctone (2), readily prepared from D-glucosamine, undergoes a rearrangement on treatment with tin(IV) chloride which leads to 3-acetamido-2-pyrone (3) and 2-acetamido-2,3-dideoxy-4,6-O-formylidene-D-threo-hex-2-enono-1,5-lact one (4). A mechanism is proposed for this unusual rearrangement, which was not observed for other analogous hex-2-enono-1,5-lactones. For example, the 2-acetoxy analog of 2 (2-acetoxy-4,6-O-benzylidene-3-deoxy-D-erythro-hex-2-enono-1,5-lactone , 7) was synthesized and treated with tin(IV) chloride affording 3-acetoxy-6-chloromethyl-2-pyrone (8) as main product. The 2-pyrone derivatives 3 and 4 are convenient precursors for the synthesis of 5-hydroxynorvaline (12) and (2S,4R,5R)-4,5,6-trihydroxynorleucine (14), respectively. The latter was prepared by diastereoselective hydrogenation of 4, followed by deprotection.
Registro:
| Documento: | Artículo |
| Título: | Synthesis of (2S,4R,5R)-4,5,6-trihydroxynorleucine and 5-hydroxynorvaline from precursors obtained by an unusual rearrangement in a 5,6-dihydro-2-pyrone |
| Autor: | Nin, A.P.; De Lederkremer, R.M.; Varela, O. |
| Filiación: | Depto. de Quimica Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, 1428, Buenos Aires, Argentina |
| Palabras clave: | 4,5,6 trihydroxynorleucine; 5 hydroxynorvaline; amino acid derivative; unclassified drug; article; chirality; drug synthesis; nuclear magnetic resonance; priority journal; reaction analysis; technique |
| Año: | 1996 |
| Volumen: | 52 |
| Número: | 40 |
| Página de inicio: | 12911 |
| Página de fin: | 12918 |
| DOI: | http://dx.doi.org/10.1016/0040-4020(96)00767-3 |
| Título revista: | Tetrahedron |
| Título revista abreviado: | TETRAHEDRON |
| ISSN: | 00404020 |
| CODEN: | TETRA |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v52_n40_p12911_Nin |
Referencias:
- Varela, O., Nin, A.P., Lederkremer, R.M., (1994) Tetrahedron Lett., 35, pp. 9359-9362
- Nin, A.P., Varela, O., Lederkremer, R.M., (1993) Tetrahedron, 49, pp. 9459-9464
- Wagner, I., Musso, H., (1983) Angew. Chem. Int. Ed. Engl., 22, pp. 816-828
- Cintas, P., (1991) Tetrahedron, 47, pp. 6079-6111
- Lederkremer, R.M., Varela, O., (1994) Adv. Carbohydr. Chem. Biochem., 50, pp. 125-209
- Horton, D., Thomson, J.K., Varela, O., Nin, A.P., Lederkremer, R.M., (1989) Carbohydr. Res., 193, pp. 49-60
- Nin, A.P., Varela, O., Lederkremer, R.M., (1991) Synthesis, pp. 73-74
- Garbish E.W., Jr., (1964) J. Am. Chem. Soc., 86, pp. 5561-5564
- Nelson, C.R., Gratzl, J.S., (1978) Carbohydr. Res., 60, pp. 267-273
- Evans, M.E., (1972) Carbohydr. Res., 21, pp. 473-475
Citas:
---------- APA ----------
Nin, A.P., De Lederkremer, R.M. & Varela, O. (1996) . Synthesis of (2S,4R,5R)-4,5,6-trihydroxynorleucine and 5-hydroxynorvaline from precursors obtained by an unusual rearrangement in a 5,6-dihydro-2-pyrone. Tetrahedron, 52(40), 12911-12918.http://dx.doi.org/10.1016/0040-4020(96)00767-3
---------- CHICAGO ----------
Nin, A.P., De Lederkremer, R.M., Varela, O. "Synthesis of (2S,4R,5R)-4,5,6-trihydroxynorleucine and 5-hydroxynorvaline from precursors obtained by an unusual rearrangement in a 5,6-dihydro-2-pyrone" . Tetrahedron 52, no. 40 (1996) : 12911-12918.http://dx.doi.org/10.1016/0040-4020(96)00767-3
---------- MLA ----------
Nin, A.P., De Lederkremer, R.M., Varela, O. "Synthesis of (2S,4R,5R)-4,5,6-trihydroxynorleucine and 5-hydroxynorvaline from precursors obtained by an unusual rearrangement in a 5,6-dihydro-2-pyrone" . Tetrahedron, vol. 52, no. 40, 1996, pp. 12911-12918.http://dx.doi.org/10.1016/0040-4020(96)00767-3
---------- VANCOUVER ----------
Nin, A.P., De Lederkremer, R.M., Varela, O. Synthesis of (2S,4R,5R)-4,5,6-trihydroxynorleucine and 5-hydroxynorvaline from precursors obtained by an unusual rearrangement in a 5,6-dihydro-2-pyrone. TETRAHEDRON. 1996;52(40):12911-12918.http://dx.doi.org/10.1016/0040-4020(96)00767-3
