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Volumn 69, Issue 9, 2004, Pages 3242-3244

Synthesis of O-Aminodihydroartemisinin via TMS Triflate Catalyzed C-O Coupling Reaction

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; OXYGEN; SOLUBILITY; SYNTHESIS (CHEMICAL); WATER;

EID: 2142812928     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0498765     Document Type: Article
Times cited : (21)

References (31)
  • 1
    • 0021948029 scopus 로고
    • (a) Klayman, D. L. Science 1985, 228, 1049-1055.
    • (1985) Science , vol.228 , pp. 1049-1055
    • Klayman, D.L.1
  • 23
    • 2142683999 scopus 로고    scopus 로고
    • note
    • 3 catalyzed C-O coupling reaction of DHA gave only a trace amount (under 10% yield) of the target product, 5D, which was judged by NMR.
  • 24
    • 0000117587 scopus 로고
    • The formation of AHA has been a problem when moderate excess of TMS triflate or TMSCI are used to activate DHA. (a) Bennek, J. A.; Gray, G. R. J. Org. Chem. 1987, 52, 892-897.
    • (1987) J. Org. Chem. , vol.52 , pp. 892-897
    • Bennek, J.A.1    Gray, G.R.2
  • 27
    • 0001183739 scopus 로고
    • 2-catalyzed C-O coupling reaction. A similar glycosylation of sugar, which was activated by TMS triflate, has been reported. Our proposed mechanism shows that the stability of the ketals (3a and 3c) and TMS ether (TMSOMe and TMSOAc, and TMSOTMS) could be responsible for the difference in the final coupling yields. (a) Tietze, L. F.; Fisher, R; Guder, H. T.; Goerlach, A.; Neumann, M.; Krach, T. Carbohydr. Res. 1987, 164, 177-194.
    • (1987) Carbohydr. Res. , vol.164 , pp. 177-194
    • Tietze, L.F.1    Fisher, R.2    Guder, H.T.3    Goerlach, A.4    Neumann, M.5    Krach, T.6
  • 29
    • 0346025403 scopus 로고    scopus 로고
    • (c) The coupling of aminosugars catalyzed by TMS triflate was doubly activated by introducing a trichloro-oxazoline group into the substrate. Donohoe, T. J.; Logan, J. G.; Laffan, D. D. P. Org. Lett. 2003, 5, 4995-4998.
    • (2003) Org. Lett. , vol.5 , pp. 4995-4998
    • Donohoe, T.J.1    Logan, J.G.2    Laffan, D.D.P.3
  • 30
    • 2142741276 scopus 로고    scopus 로고
    • note
    • (d) The real catalyst may be triflic acid after TMS triflate is consumed.
  • 31
    • 2142735697 scopus 로고    scopus 로고
    • note
    • Compound 8 was soluble in neutral (pH = 7.35) phosphate buffer (<3 mg/mL).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.