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Volumn 46, Issue 19, 2005, Pages 3291-3295

Chemo-enzymatic short-step total synthesis of symbioramide

Author keywords

Aminolysis; Dihydrosphingosine; Lipase; Symbioramide; Hydroxy acid

Indexed keywords

CERAMIDE DERIVATIVE; SYMBIORAMIDE; UNCLASSIFIED DRUG;

EID: 17244373479     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.093     Document Type: Article
Times cited : (20)

References (24)
  • 8
    • 85030801472 scopus 로고    scopus 로고
    • Jpn. Kokai Tokkyo Koho 2001, JP 2001039973 (CA 134:162911)
    • Tomitani, K.; Sato, K.; Takahashi, H. Jpn. Kokai Tokkyo Koho 2001, JP 2001039973 (CA 134:162911)
    • Tomitani, K.1    Sato, K.2    Takahashi, H.3
  • 10
    • 85030796707 scopus 로고    scopus 로고
    • note
    • 1H NMR: (E) δ 5.47 (dd); (Z) δ 5.35-5.41 (m)
  • 11
    • 85030801350 scopus 로고    scopus 로고
    • note
    • 3: C, 73.03; H, 11.61. Found: C, 73.15; H, 11.52
  • 13
    • 85030804774 scopus 로고    scopus 로고
    • note
    • 3) δ 0.88 (t, 3H, J 6.8 Hz), 1.23 (br s, 24H), 2.03 (dt, 2H, J 7.0, 7.0 Hz), 2.87 (br s, 1H), 3.77 (s, 3H), 4.58 (d, 1H, J 5.9 Hz), 5.47 (dd, 1H, J 5.9, 15.1 Hz), 5.86 (dt, 1H, J 15.1, 7.0 Hz)
  • 14
    • 85030800219 scopus 로고    scopus 로고
    • note
    • 3: C, 72.44; H, 11.48. Found: C, 72.52; H, 11.39. The hydrolysis proceeded in non-enantioselective manner. Also the epoxy ester (±)-4 was a good substrate for Chirazyme L-2, to give the epoxy acid (quant.)
  • 15
    • 0026045467 scopus 로고
    • T. Sugai, and H. Ohta Tetrahedron Lett. 32 1991 7063 7064 Long chain α-hydroxy acid is superior to methyl and benzyl esters to acquire higher enantioselectivity in resolution
    • (1991) Tetrahedron Lett. , vol.32 , pp. 7063-7064
    • Sugai, T.1    Ohta, H.2
  • 16
    • 85030804899 scopus 로고    scopus 로고
    • note
    • 3), 5.51 (d, 1H, J 15.1, 7.3 Hz, H-3), 5.58 (d, 1H, J 7.3 Hz, H-2), 5.86 (dt, 1H, J 15.1, 7.0 Hz, H-4)
  • 17
    • 85030803426 scopus 로고    scopus 로고
    • note
    • 13C NMR δ 52.82, 65.92, 72.31, 169.74
  • 20
    • 2642525045 scopus 로고    scopus 로고
    • Lipase-catalyzed aminolysis in organic solvent, review: I. Alfonso, and V. Gotor Chem. Soc. Rev. 33 2004 201 209
    • (2004) Chem. Soc. Rev. , vol.33 , pp. 201-209
    • Alfonso, I.1    Gotor, V.2
  • 24
    • 85030801467 scopus 로고    scopus 로고
    • note
    • 3)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.