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
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 (...
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| Otros Autores: | , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
Elsevier Ltd
1996
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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 |
| LEADER | 04395caa a22006017a 4500 | ||
|---|---|---|---|
| 001 | PAPER-3498 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203257.0 | ||
| 008 | 190411s1996 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0030607169 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a TETRA | ||
| 100 | 1 | |a Nin, A.P. | |
| 245 | 1 | 0 | |a 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 |
| 260 | |b Elsevier Ltd |c 1996 | ||
| 270 | 1 | 0 | |m Varela, O.; Departamento de Quimica Organica, Facultad Ciencias Exactas/Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Varela, O., Nin, A.P., Lederkremer, R.M., (1994) Tetrahedron Lett., 35, pp. 9359-9362 | ||
| 504 | |a Nin, A.P., Varela, O., Lederkremer, R.M., (1993) Tetrahedron, 49, pp. 9459-9464 | ||
| 504 | |a Wagner, I., Musso, H., (1983) Angew. Chem. Int. Ed. Engl., 22, pp. 816-828 | ||
| 504 | |a Cintas, P., (1991) Tetrahedron, 47, pp. 6079-6111 | ||
| 504 | |a Lederkremer, R.M., Varela, O., (1994) Adv. Carbohydr. Chem. Biochem., 50, pp. 125-209 | ||
| 504 | |a Horton, D., Thomson, J.K., Varela, O., Nin, A.P., Lederkremer, R.M., (1989) Carbohydr. Res., 193, pp. 49-60 | ||
| 504 | |a Nin, A.P., Varela, O., Lederkremer, R.M., (1991) Synthesis, pp. 73-74 | ||
| 504 | |a Garbish E.W., Jr., (1964) J. Am. Chem. Soc., 86, pp. 5561-5564 | ||
| 504 | |a Nelson, C.R., Gratzl, J.S., (1978) Carbohydr. Res., 60, pp. 267-273 | ||
| 504 | |a Evans, M.E., (1972) Carbohydr. Res., 21, pp. 473-475 | ||
| 520 | 3 | |a 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. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, EX-173 | ||
| 536 | |a Detalles de la financiación: Acknowledgements. We thank the University of Buenos Aires (grant EX-173) and CONICET (Consejo National de Investigaciones Cientificas y Tecnicas) for financial support, and UMYMFOR (CONICET-FCEN-UBA) for the microanalyses. 0. V. and R. M. L. are Research Members of CONICET. | ||
| 593 | |a Depto. de Quimica Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, 1428, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 4,5,6 TRIHYDROXYNORLEUCINE |
| 690 | 1 | 0 | |a 5 HYDROXYNORVALINE |
| 690 | 1 | 0 | |a AMINO ACID DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHIRALITY |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a REACTION ANALYSIS |
| 690 | 1 | 0 | |a TECHNIQUE |
| 700 | 1 | |a De Lederkremer, R.M. | |
| 700 | 1 | |a Varela, O. | |
| 773 | 0 | |d Elsevier Ltd, 1996 |g v. 52 |h pp. 12911-12918 |k n. 40 |p TETRAHEDRON |x 00404020 |w (AR-BaUEN)CENRE-45 |t Tetrahedron | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0030607169&doi=10.1016%2f0040-4020%2896%2900767-3&partnerID=40&md5=70ddfb7ff5d5a4ff13b59059430ef3fa |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/0040-4020(96)00767-3 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00404020_v52_n40_p12911_Nin |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v52_n40_p12911_Nin |y Registro en la Biblioteca Digital |
| 961 | |a paper_00404020_v52_n40_p12911_Nin |b paper |c PE | ||
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| 963 | |a VARI | ||
| 999 | |c 64451 | ||