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Volumn 4, Issue 7, 2002, Pages 1055-1057

Diastereoselective Synthesis of ψ[(E)-CMe=CH]- and ψ[(E)-CMe=CMe]-Type Dipeptide Isosteres Based on Organocopper-mediated anti-SN2′ Reaction

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; DIPEPTIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ORGANOMETALLIC COMPOUND;

EID: 0037018473     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016835b     Document Type: Article
Times cited : (16)

References (32)
  • 14
    • 0000219483 scopus 로고
    • Peptide Secondary Structure Mimetics
    • Symposia-in-print, no. 50; Kahn, M., Ed.
    • For recent reviews of peptidomimetics, see: (a) Peptide Secondary Structure Mimetics. Tetrahedron (Symposia-in-print, no. 50; Kahn, M., Ed.) 1993, 49, 3444.
    • (1993) Tetrahedron , vol.49 , pp. 3444
  • 29
    • 0030768536 scopus 로고    scopus 로고
    • D-Phenylalanine derivatives 1 and 6 were utilized for the synthesis of D-Phe-ψ[(E)-CMe=CX]-D/L-Val-type EADIs as a model case in this communication. A dipeptide. D-Phe-L-Val, accommodates in the (i + 1)-(i + 2) position in the type II′ β-turn substructure of the cyclic RGD pentapeptide, cyclo(-Arg-Gly-Asp-D-Phe-Val-), previously reported: Haubner, R.; Finsinger, D.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1374.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1374
    • Haubner, R.1    Finsinger, D.2    Kessler, H.3
  • 30
    • 0042905282 scopus 로고    scopus 로고
    • note
    • The diastereomerically pure allyl alcohols 4a and 5a,b were readily purified by recrystallization from the diastereomixture, respectively. The syn-allyl alcohol 4b could not be isolated in this step, and thus the diastereomixture, which contained the syn-allyl alcohol 4b as a major isomer, was converted into the corresponding oxazolidin-2-one derivative 8b. The diastereomerically pure oxazolidin-2-one 8b was purified by recrystallization.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.