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Volumn 75, Issue 5, 2010, Pages 1386-1392

An efficient preparation of N-Methyl-α-amino acids from N-Nosyl-α-amino acid phenacyl esters

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DIAZOMETHANES; MOLAR EXCESS; PEPTIDE SYNTHESIS; PROTECTING GROUP; SIDE CHAINS; SOLID-PHASE; SOLUTION PHASE SYNTHESIS; SYNTHETIC STRATEGIES;

EID: 77949285279     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo901643f     Document Type: Article
Times cited : (15)

References (34)
  • 14
    • 18744415178 scopus 로고    scopus 로고
    • DiGioia, M. L.; Leggio, A.; Liguori, A. J. Org. Chem. 2005, 70, 3892. For previously reported N-methylation methods see also the references cited therein.
    • DiGioia, M. L.; Leggio, A.; Liguori, A. J. Org. Chem. 2005, 70, 3892. For previously reported N-methylation methods see also the references cited therein.
  • 15
    • 53549135850 scopus 로고    scopus 로고
    • In Houben-Weyl Methods of Organic Chemistry
    • Goodman, M, Felix, A, Moroder, L, Toniolo, C, Eds, Georg Thieme Verlag: Stuttgart, Germany, and references cited therein
    • a) Gilon, C.; Dechantsreiter, M. A.; Burkhart, F.; Friedler, A.; Kessler, H. In Houben-Weyl Methods of Organic Chemistry, Vol E22c, Synthesis of Peptides and Peptidomimetics; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.; Georg Thieme Verlag: Stuttgart, Germany, 2002; pp 215-291 and references cited therein,
    • (2002) Synthesis of Peptides and Peptidomimetics , vol.E22c , pp. 215-291
    • Gilon, C.1    Dechantsreiter, M.A.2    Burkhart, F.3    Friedler, A.4    Kessler, H.5
  • 30
    • 77949295868 scopus 로고    scopus 로고
    • Arndt, F. Org. Synth. 1943, 2, 165. Diazomethane is dangerous because, in the presence of relatively acid protons, it forms the methyl diazonium ion that could methylate the alcoholic hydroxyl, amino, thiol, and carboxyl functions of biological structures. Diazomethane is explosive when it is prepared by distillation and used in hydrocarbon solvents which cannot solvate it. Commercially available trimethylsilyldiazomethane was also used as a methylating agent as a safe substitute for diazomethane (ref 3g).
    • Arndt, F. Org. Synth. 1943, 2, 165. Diazomethane is dangerous because, in the presence of relatively acid protons, it forms the methyl diazonium ion that could methylate the alcoholic hydroxyl, amino, thiol, and carboxyl functions of biological structures. Diazomethane is explosive when it is prepared by distillation and used in hydrocarbon solvents which cannot solvate it. Commercially available trimethylsilyldiazomethane was also used as a methylating agent as a safe substitute for diazomethane (ref 3g).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.