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Volumn 55, Issue 24, 1999, Pages 7589-7600

Application of 2,3-aziridino-γ-lactone methodology toward the enantiospecific synthesis of the (3S,4S)-isomer of dihydroxy-L-glutamic acid

Author keywords

Azides; Aziridines; Glutamic acid; Lactones

Indexed keywords

AZIRIDINE DERIVATIVE; BENZYL ALCOHOL; BORON DERIVATIVE; FLUORIDE; GAMMA BUTYROLACTONE; GAMMA LACTONE DERIVATIVE; GLUTAMIC ACID DERIVATIVE; RIBOSE;

EID: 0033546425     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00405-6     Document Type: Article
Times cited : (32)

References (49)
  • 9
    • 0003772393 scopus 로고
    • Watkins, J.C.; Collingridge, G.L., Eds.; IRL Press at Oxford University Press : Oxford
    • (a) Watkins, J.C. In The NMDA Receptor ; Watkins, J.C.; Collingridge, G.L., Eds.; IRL Press at Oxford University Press : Oxford, 1989.
    • (1989) The NMDA Receptor
    • Watkins, J.C.1
  • 35
    • 0027446387 scopus 로고
    • Synthesis and reactivity of 2,3-aziridino-γ-lactones : (a) Dubois, L.; Dodd, R.H. Tetrahedron 1993, 49, 901.
    • (1993) Tetrahedron , vol.49 , pp. 901
    • Dubois, L.1    Dodd, R.H.2
  • 44
    • 0027363856 scopus 로고
    • The use of catalytic 1,3-propanedithiol in the presence of sodium borohydride has been reported to efficiently reduce azide groups. However, chemoselectivities of this methodology were not reported and consequently no attempt was made to apply this technique to compound 16. See : Pei, Y.; Wickham, B.O.S. Tetrahedron Lett. 1993, 34, 7509.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7509
    • Pei, Y.1    Wickham, B.O.S.2
  • 48
    • 33646329742 scopus 로고    scopus 로고
    • note
    • 13C NMR of compound 3 showed the presence of a mixture of diastereomers which would result from partial or complete epimerisation of one or more of the three chiral centers. Within the limits of detection of impurities by NMR, compound (3S,4S)-3 can thus be considered to be >95% pure.
  • 49
    • 33847530141 scopus 로고    scopus 로고
    • A preliminary study of the pharmacological activity of (3S,4S)-3 with respect to glutamate receptors will be reported elsewhere
    • A preliminary study of the pharmacological activity of (3S,4S)-3 with respect to glutamate receptors will be reported elsewhere.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.