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Volumn 47, Issue 49, 2006, Pages 8777-8780

An intramolecular conjugate addition of γ-trichloroacetimidoyloxy-α,β-unsaturated esters: a very concise route to daunosamine, acosamine, ristosamine and 3-epi-daunosamine precursors

Author keywords

3 Amino 2,3,6 trideoxyhexose; Deoxyamino sugar; Intramolecular conjugate addition; Oxazoline; Trichloroacetimidate

Indexed keywords

ACOSAMINE; DAUNOSAMINE; DAUNOSAMINE DERIVATIVE; ESTER DERIVATIVE; OXAZOLINE DERIVATIVE; RISTOSAMINE; UNCLASSIFIED DRUG;

EID: 33750442566     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.164     Document Type: Article
Times cited : (19)

References (21)
  • 6
    • 0141632609 scopus 로고    scopus 로고
    • For a recent synthesis of 3-amino-2,3,6-trideoxyhexoses, see: and references cited therein
    • For a recent synthesis of 3-amino-2,3,6-trideoxyhexoses, see:. Ginesta X., Pastó M., Pericàs M.A., and Riera A. Org. Lett. 5 (2003) 3001-3004 and references cited therein
    • (2003) Org. Lett. , vol.5 , pp. 3001-3004
    • Ginesta, X.1    Pastó, M.2    Pericàs, M.A.3    Riera, A.4
  • 8
    • 29544445868 scopus 로고    scopus 로고
    • Intramolecular conjugate addition of trichloroacetimidates in a cyclic system was very recently reported, see:
    • Intramolecular conjugate addition of trichloroacetimidates in a cyclic system was very recently reported, see:. Brown J.R., Nishimura Y., and Esko J.D. Bioorg. Med. Chem. Lett. 16 (2006) 532-536
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 532-536
    • Brown, J.R.1    Nishimura, Y.2    Esko, J.D.3
  • 9
    • 0001417001 scopus 로고
    • For the intramolecular conjugate addition of trichloroacetimidates to vinyl sulfones, see:
    • For the intramolecular conjugate addition of trichloroacetimidates to vinyl sulfones, see:. Li X.C., and Fuchs P.L. Synlett (1994) 629-630
    • (1994) Synlett , pp. 629-630
    • Li, X.C.1    Fuchs, P.L.2
  • 11
    • 33750464344 scopus 로고    scopus 로고
    • note
    • H-2 5.95 (dd, J = 1.5, 15.8 Hz)].
  • 12
    • 33750446124 scopus 로고    scopus 로고
    • note
    • All new compounds were fully characterised with relevant spectroscopic data and elemental analyses.
  • 13
    • 33750447120 scopus 로고    scopus 로고
    • note
    • 4Si: C 44.40; H 6.52; N 3.24. Found: C 44.63; H 6.55; N 3.09.
  • 14
    • 33750453562 scopus 로고    scopus 로고
    • note
    • In the case of the carbamate-mediated conjugate additions, tert-BuOK was used as the most effective base, while DBU was not reported, see: Ref. 7 and references cited therein.
  • 16
    • 0000012858 scopus 로고
    • 1H-coupling constants for trans (6.0-7.5 Hz) and cis (10.0-11.2 Hz) compounds was also investigated in the cases of 2-phenyl-2-oxazoline derivatives, see:
    • 1H-coupling constants for trans (6.0-7.5 Hz) and cis (10.0-11.2 Hz) compounds was also investigated in the cases of 2-phenyl-2-oxazoline derivatives, see:. Futagawa S., Inui T., and Shiba T. Bull. Chem. Soc. Jpn. 46 (1973) 3308-3310
    • (1973) Bull. Chem. Soc. Jpn. , vol.46 , pp. 3308-3310
    • Futagawa, S.1    Inui, T.2    Shiba, T.3
  • 17
    • 33750447803 scopus 로고    scopus 로고
    • note
    • The irradiation of methyne hydrogen adjacent to the methyl group on the compound 3a yielded an NOE of ca. 16% on H-4′ along with H-5′, while no NOE was observed on the methylene protons (H-2). On the contrary, the irradiation of the hydrogen corresponding to compound 3b yielded an NOE of ca. 3% on the one methylene protons (H-2), while a relatively small NOE (<1%) was observed on H-4′.
  • 21
    • 33750468133 scopus 로고    scopus 로고
    • note
    • For hydrolysis of the similar racemic oxazolines and subsequent manipulations, see: Ref. 14.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.