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Volumn 6, Issue 17, 2004, Pages 2929-2932

Assembling heterocycle-tethered C-glycosyl and α-amino acid residues via 1,3-dipolar cycloaddition reactions

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE; ALPHA AMINO ACID; AMINO ACID DERIVATIVE; AZIDE; CARBON GLYCOSYLAMINO ACID; ISOXAZOLE DERIVATIVE; OXIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 4444268846     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048963g     Document Type: Article
Times cited : (144)

References (39)
  • 4
    • 0001094662 scopus 로고    scopus 로고
    • (b) Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
    • (1996) Chem. Rev. , vol.96 , pp. 683-720
    • Dwek, R.A.1
  • 16
    • 0004101860 scopus 로고
    • Wiley: New York
    • For reviews, see: (a) Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; Wiley: New York, 1984. (b) Padwa, A.; Pearson, W. H. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Wiley: New York, 2003.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry
    • Padwa, A.1
  • 21
    • 0036992603 scopus 로고    scopus 로고
    • C-Glycosyl nitrile oxides: (a) Baker, K. W. J.; March, A. R.; Parsons, S.; Paton, M.; Stewart, G. W. Tetrahedron 2002, 58, 8505-8513. (b) Dondoni, A.; Giovannini, P. P. Synthesis 2002, 1701-1706.
    • (2002) Synthesis , pp. 1701-1706
    • Dondoni, A.1    Giovannini, P.P.2
  • 22
    • 0032911810 scopus 로고    scopus 로고
    • Ethynyl C-glycosides: (a) Nishika, T.; Ishikawa, M.; Isobe, M. Synlett 1999, 123-125. (b) Dondoni, A.; Mariotti, G.; Marra, A. J. Org. Chem. 2002, 67, 4475-4486.
    • (1999) Synlett , pp. 123-125
    • Nishika, T.1    Ishikawa, M.2    Isobe, M.3
  • 23
    • 0037189230 scopus 로고    scopus 로고
    • Ethynyl C-glycosides: (a) Nishika, T.; Ishikawa, M.; Isobe, M. Synlett 1999, 123-125. (b) Dondoni, A.; Mariotti, G.; Marra, A. J. Org. Chem. 2002, 67, 4475-4486.
    • (2002) J. Org. Chem. , vol.67 , pp. 4475-4486
    • Dondoni, A.1    Mariotti, G.2    Marra, A.3
  • 30
    • 0142011019 scopus 로고    scopus 로고
    • and references therein
    • 13C NMR spectral data of 1,4- and 1,5-disubstituted triazoles, see: Crandall. J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045-2047. Katritzky, A. R.; Lagowski, J. M. In Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon Press: Oxford, 1984; pp 15-16.
    • (2003) Chem. Commun. , pp. 2450-2451
    • Wang, Z.-X.1    Qin, H.-L.2
  • 31
    • 0000777334 scopus 로고
    • 13C NMR spectral data of 1,4- and 1,5-disubstituted triazoles, see: Crandall. J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045-2047. Katritzky, A. R.; Lagowski, J. M. In Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon Press: Oxford, 1984; pp 15-16.
    • (1975) J. Org. Chem. , vol.40 , pp. 2045-2047
    • Crandall, J.K.1    Crawley, L.C.2    Komin, J.B.3
  • 32
    • 0000764131 scopus 로고
    • Potts, K. T., Ed.; Pergamon Press: Oxford
    • 13C NMR spectral data of 1,4- and 1,5-disubstituted triazoles, see: Crandall. J. K.; Crawley, L. C.; Komin, J. B. J. Org. Chem. 1975, 40, 2045-2047. Katritzky, A. R.; Lagowski, J. M. In Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon Press: Oxford, 1984; pp 15-16.
    • (1984) Comprehensive Heterocyclic Chemistry , pp. 15-16
    • Katritzky, A.R.1    Lagowski, J.M.2
  • 33
    • 4444336194 scopus 로고    scopus 로고
    • note
    • Attempts to carry out the one-pot oxidative cleavage of the oxazolidine ring with the Jones reagent as described (see ref 12b) turned out to be fruitless.
  • 37
    • 0000873466 scopus 로고
    • Crucial for the selective hydrogenolysis of benzyl groups in 18a was the presence of acetic acid in the reaction medium. For a wider discussion on the effect of pH in the hydrogenation of isoxazole derivatives, see: Stork, G.; Danishefsky, S.; Ohashi, M. J. Am. Chem. Soc. 1967, 89, 5459-5460.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 5459-5460
    • Stork, G.1    Danishefsky, S.2    Ohashi, M.3
  • 38
    • 4444248552 scopus 로고    scopus 로고
    • note
    • A prolonged reaction time caused partial epimerization at the α-carbon of the target C-glycosyl α-amino acids.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.