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Volumn 12, Issue 9, 2010, Pages 1924-1927

Chemoselective protection of α-Ketoacids by direct annulations with oximes

Author keywords

[No Author keywords available]

Indexed keywords

ACID; OXIME;

EID: 77951856368     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100467t     Document Type: Article
Times cited : (13)

References (27)
  • 9
    • 77951859505 scopus 로고    scopus 로고
    • For recent work on the preparation of N-terminal peptide hydroxylamines, see
    • For recent work on the preparation of N-terminal peptide hydroxylamines, see
  • 11
    • 65949106377 scopus 로고    scopus 로고
    • Note
    • We have recently disclosed a sulfur ylide-based linker for the solid phase synthesis of C-terminal α-ketoacid peptides. While this protocol works well for many complex, unprotected peptides it is not appropriate for simpler ketoacids or for peptides with cysteine or methionine residues: Ju, L.; Bode, J. W. Org. Biomol. Chem. 2009, 7, 2259
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 2259
    • Ju, L.1    Bode, J.W.2
  • 20
    • 77951807253 scopus 로고    scopus 로고
    • Note
    • 2O, rt). We do not detect the 2,5-dihydrooxazole 3-oxide as an intermediate.
  • 21
    • 77951782027 scopus 로고    scopus 로고
    • The use of additives such as Lewis acids or dehydrating reagents did not significantly improve yield
    • The use of additives such as Lewis acids or dehydrating reagents did not significantly improve yield.
  • 24
    • 0017591592 scopus 로고
    • For similar deprotection conditions on a side-chain unprotected peptide, see
    • For similar deprotection conditions on a side-chain unprotected peptide, see: Veber, D. F.; Paleveda, W. J., Jr.; Lee, Y. C.; Hirschmann, R. J. Org. Chem. 1977, 42, 3286-3288
    • (1977) J. Org. Chem. , vol.42 , pp. 3286-3288
    • Veber, D.F.1    Paleveda Jr., W.J.2    Lee, Y.C.3    Hirschmann, R.4
  • 25
    • 77951870496 scopus 로고    scopus 로고
    • Note
    • Despite the ring-chain tautomerization, this α-ketoacid may be used for decarboxylative condensation with an N -alkylhydroxylamine. See Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.