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Volumn 62, Issue 13, 1997, Pages 4277-4284

2,3-Aziridino-2,3-dideoxy-D-ribono-γ-lactone 5-Phosphonate: Stereocontrolled Synthesis from D-Lyxose and Unusual Aziridine Ring Opening

Author keywords

[No Author keywords available]

Indexed keywords

2,3 AZIRIDINO 2,3 DIDEOXYRIBONOLACTONE 5 PHOSPHONIC ACID; AZIRIDINE DERIVATIVE; N (BENZYLOXYCARBONYL) 4 (DIETHOXYPHOSPHINYL)METHYL 3 OXA 6 AZABICYCLO[3.1.0]HEXAN 2 ONE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030861232     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9623494     Document Type: Article
Times cited : (28)

References (36)
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    • For reviews, see: Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Trends Pharmacol. Sci. 1990, 11, 25. Nakanishi, S. Science 1992, 258, 597. Bigge, C. F. Biochem. Pharmacol. 1993, 45, 1547. Kalb, R. G. Neuroscientist 1995, 1, 60.
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    • Bigge, C.F.1
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    • For reviews, see: Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Trends Pharmacol. Sci. 1990, 11, 25. Nakanishi, S. Science 1992, 258, 597. Bigge, C. F. Biochem. Pharmacol. 1993, 45, 1547. Kalb, R. G. Neuroscientist 1995, 1, 60.
    • (1995) Neuroscientist , vol.1 , pp. 60
    • Kalb, R.G.1
  • 5
    • 0003772393 scopus 로고
    • Watkins, J. C., Collingridge, G. L., Eds.; IRL Press at Oxford University Press: Oxford
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    • (1989) The NMDA Receptor
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    • 0020516359 scopus 로고
    • Meldrum, B. S.; Croucher, M. J.; Czuczwar, S. J.; Collins, J. F.; Curry, K.; Joseph, M.; Stone, T. W. Neuroscience 1983, 9, 925. Lehmann, J.; Schneider, J.; McPherson, S.; Murphy, D. E.; Bernard, P.; Tsai, C.; Bennett, D. A.; Pastor, G.; Steel, D. J.; Boehm, C.; Cheney, D. L.; Liebman, J. M.; Williams, M.; Wood, P. L. J. Pharmacol. Exp. Ther. 1987, 240, 737.
    • (1983) Neuroscience , vol.9 , pp. 925
    • Meldrum, B.S.1    Croucher, M.J.2    Czuczwar, S.J.3    Collins, J.F.4    Curry, K.5    Joseph, M.6    Stone, T.W.7
  • 28
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    • Adapted from the procedure for the preparation of the ribo analogue of 6: Levene, P. A.; Stiller, E. T. J. Biol. Chem. 1934, 104, 299.
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    • note
    • N2 nucleophilic opening of the aziridine ring at C-3, to give the trans-2-amino-3-alkoxybutyro-lactone derivative, with no participation by the C-5 phosphonate group. Details of this work will be published elsewhere.
  • 36
    • 0027517214 scopus 로고
    • Although unusual, this intramolecular aziridine ring opening is not entirely unprecedented since Ho and co-workers have described such a reaction with a benzyl ester group or a carboxamide. Ho, M.; Chung, J. K. K.; Tang, N. Tetrahedron Lett. 1993, 34, 6513.
    • (1993) Tetrahedron Lett , vol.34 , pp. 6513
    • Ho, M.1    Chung, J.K.K.2    Tang, N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.