Synthesis and transformations of (1R,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O- isopropylidene-1,2,3-cyclopentanetriol: Synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3- cyclopentanetriol

Tetrahedron Asymmetry

Volumn 8, Issue 13, 1997, Pages 2249-2256

  Marco Contelles, José ^a   Rodríguez Fernández, Ma Mercedes ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; POLYOL;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343036149     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00236-X     Document Type: Article

References (23)

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2. (b) Marco-Contelles, J.; Ruiz, P.; Martínez, L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669.
3. (a) Marco-Contelles, J.; Bernabé, M. Tetrahedron Lett. 1994, 35, 6361.
4. (b) Marco-Contelles, J.; Destabel, C.; Gallego, P.; Chiara, J. L.; Bernabé, M. J. Org. Chem. 1996, 61, 1354.
5. (c) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
6. Márquez, V. E.; Lim, M. J. Med. Res. Rev. 1986, 6, 1.
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8. (b) Bedes, J.; Sáji, G.; Tömösközi, I.; Gonber, N.; Gulácsi, E.; Ötvös, L. Tetrahedron Lett. 1988, 29, 2861.
9. Arita, M.; Adeihi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4949.
10. Yoshikawa, M.; Okaichi, Y.; Cha, B. Ch.; Kitagawe, I. Tetrahedron 1990, 46, 7549.
11. (a) Wilcox, C. S.; Thomasco, L. M. J. Org. Chem. 1985, 50, 546.
12. (b) Bartlett, P. A.; McLaren, K. L.; Ting, P. C. J. Am. Chem. Soc. 1988, 100, 1633.
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14. See also: Ingall, A.H.; Moore, P. R.; Roberts, S. M. Chem. Commun. 1994, 83; (Corrigenda: Chem. Commun. 1994, 675)
15. (a) Siddiqi, S. M.; Chen, X.; Schneller, S. W. J. Med. Chem. 1994, 37, 1382.
16. (b) Siddiqi, S. M.; Chen, X.; Schneller, S. W. J. Med. Chem. 1994, 37, 551, and references cited therein.
17. More correctly: (3aα4β6α,6aα)-6-aminotetrahydro-2,2-dimethyl-4H- cyclopenta-1,3-dioxol-4-ol.
18. (a) Patil, S. D.; Schneller, S. W.; Hosoya, M.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1992, 35, 3372.
19. (b) Patil, S. D.; Schneller, S. W. J. Heterocyclic Chem. 1991, 28, 823.
20. Jung, M.; Offenbächer, G.; Rétey, J. Helv. Chim. Acta 1983, 66, 1915.
21. 3). We think this value should probably be amended.
22. Mitsunobu, O. Synthesis 1981, 1.
23. Chiara, J. L.; Destabel, C.; Gallego, P.; Marco-Contelles, J. J. Org. Chem. 1996, 61, 359.