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Volumn 37, Issue 24, 1996, Pages 4237-4240

Reaction of N-trityl amino acids with BOP: Efficient synthesis of t-butyl esters as well as N-trityl serine- and threonine-β-lactones

Author keywords

[No Author keywords available]

Indexed keywords

BUTYLAMINE; LACTONE DERIVATIVE; PEPTIDE; SERINE DERIVATIVE; TERT BUTYL ALCOHOL; THREONINE;

EID: 0029981008     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00805-2     Document Type: Article
Times cited : (30)

References (25)
  • 2
    • 0025880705 scopus 로고
    • Bol, K.M.; Liskamp, R.M.J. Tetrahedron Lett. 1991, 52, 5401-5404; Bol, K.M.; Liskamp, R.M.J. Tetrahedron 1992, 48, 6425-6438.
    • (1991) Tetrahedron Lett. , vol.52 , pp. 5401-5404
    • Bol, K.M.1    Liskamp, R.M.J.2
  • 3
    • 0026760304 scopus 로고
    • Bol, K.M.; Liskamp, R.M.J. Tetrahedron Lett. 1991, 52, 5401-5404; Bol, K.M.; Liskamp, R.M.J. Tetrahedron 1992, 48, 6425-6438.
    • (1992) Tetrahedron , vol.48 , pp. 6425-6438
    • Bol, K.M.1    Liskamp, R.M.J.2
  • 6
    • 85030200376 scopus 로고    scopus 로고
    • note
    • +.
  • 9
    • 0000898966 scopus 로고
    • thereby dismissing the incorrect structure of a HOBt amide in the former reference
    • b) Papaioannou, D.; Athanassopoulos, C.; Magafa, V.; Karigiannis, G.; Karamanos, N.; Stavropoulos, G.; Napoli, A.; Sindona, G.; Aksnes, D.W.; Francis, G.W.; Aaberg, A. Acta. Chem. Scand. 1995, 49, 103-114. Although not cited in this latter reference, it was apparantly possible to prepare, using DCC/HOBt, and to obtain a crystal structure of the HOBt amide of N-trityl methionine (Barlos, K.; Papaioannou, D.; Voliotis, S.; Prewo, R.; Bieri, J.H. J. Org. Chem. 1985, 50, 696-697), thereby dismissing the incorrect structure of a HOBt amide in the former reference.
    • (1985) J. Org. Chem. , vol.50 , pp. 696-697
    • Barlos, K.1    Papaioannou, D.2    Voliotis, S.3    Prewo, R.4    Bieri, J.H.5
  • 11
    • 33845280670 scopus 로고
    • The terms "armed" and "disarmed", albeit used in a different way, were introduced by Fraser-Reid et al. in carbohydrate chemistry to indicate the effect of a particular C2-oxygen protective group on glycosylation: Mootoo, D.R.; Konradson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583-5584.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5583-5584
    • Mootoo, D.R.1    Konradson, P.2    Udodong, U.3    Fraser-Reid, B.4
  • 14
    • 0027931547 scopus 로고
    • In contrast, the corresponding Boc-protected ynone could be prepared in 90% yield: Overhand, M.; Hecht, S.M. J. Org. Chem. 1994, 59, 4721-4722.
    • (1994) J. Org. Chem. , vol.59 , pp. 4721-4722
    • Overhand, M.1    Hecht, S.M.2
  • 15
    • 85030198550 scopus 로고    scopus 로고
    • note
    • -1 (C=O). m.p. 139-142 °C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.