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Volumn 74, Issue 2, 2009, Pages 685-695

Divergent synthesis of three classes of aryl N-glycosides by solvent control

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRAQUINONE DERIVATIVES; ARYL GLYCOSIDES; BIOLOGICAL APPLICATIONS; C-GLYCOSIDES; DIVERGENT SYNTHESIS; GLYCOSYL AZIDES; GLYCOSYLATED; HETEROCYCLIC COMPOUNDS; NAPHTHOQUINONE; O-GLYCOSIDES; POLAR SOLVENTS; SOLVENT CONTROLS;

EID: 60849100798     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8020133     Document Type: Article
Times cited : (31)

References (45)
  • 6
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    • U.S. Patent No. 4,758,561
    • Baut, L. et al. U.S. Patent No. 4,758,561.
    • Baut, L.1
  • 10
    • 64549094552 scopus 로고    scopus 로고
    • Sum, F.-W, Dusza, J, Santos, E. D, Grosu, G, Reich, M, Du, X.;
    • Sum, F.-W.; Dusza, J.; Santos, E. D.; Grosu, G.; Reich, M.; Du, X.;
  • 15
  • 16
    • 0346768307 scopus 로고    scopus 로고
    • Ed, Wiley-VCH: Weinheim, Germany
    • Wong, C.-H., Ed. Carbohydrate-Based Drug Discovery; Wiley-VCH: Weinheim, Germany, 2003.
    • (2003) Carbohydrate-Based Drug Discovery
  • 18
    • 64349101955 scopus 로고    scopus 로고
    • Frontiers in Carbohydrate Chemistry
    • Demchenko, A., Ed.; Frontiers in Carbohydrate Chemistry; ACS Symposium Series; Vol. 960, 2007.
    • (2007) ACS Symposium Series , vol.960
    • Demchenko, A.1    Ed2
  • 22
    • 0025952771 scopus 로고    scopus 로고
    • For examples of O-aryl glycosides, see: (a) Roush, W. R, Lin, X.-F. J Org. Chem. 1991, 56, 5740-5742
    • For examples of O-aryl glycosides, see: (a) Roush, W. R.; Lin, X.-F. J Org. Chem. 1991, 56, 5740-5742.
  • 24
    • 64549133735 scopus 로고    scopus 로고
    • For examples of C-aryl glycosides, see: (a) Hart, D. J, Leroy, V, Merriman, G. H, Young, D. G. J. J. Org. Chem. 1992, 57, 670-5680
    • For examples of C-aryl glycosides, see: (a) Hart, D. J.; Leroy, V.; Merriman, G. H.; Young, D. G. J. J. Org. Chem. 1992, 57, 670-5680.
  • 31
    • 34047131110 scopus 로고    scopus 로고
    • For examples of N-aryl glycosides, see: (a) Bridiau, N, Benmansour, M, Legoy, M. D, Maugard, T. Tetrahedron 2007, 63, 4178-4183
    • For examples of N-aryl glycosides, see: (a) Bridiau, N.; Benmansour, M.; Legoy, M. D.; Maugard, T. Tetrahedron 2007, 63, 4178-4183.
  • 41
    • 64549146144 scopus 로고    scopus 로고
    • With the exception of 15m and 17m, the separation of 15/17 mixture proves to be challenging. However, for the acetylation of the mixture followed by aqueous workup, we were amazed to discover that only the 17 component was present in organic solution. Further purification of 17 by recrystallization offered the pure desired products
    • With the exception of 15m and 17m, the separation of 15/17 mixture proves to be challenging. However, for the acetylation of the mixture followed by aqueous workup, we were amazed to discover that only the 17 component was present in organic solution. Further purification of 17 by recrystallization offered the pure desired products.
  • 42
    • 64549135002 scopus 로고    scopus 로고
    • Among the samples, 19a, 19d, 19f, 19k, 19m, submitted for one-dose assay, 19f and 19k were selected for further five-dose testing. Please refer to Supporting Information for more details.
    • Among the samples, 19a, 19d, 19f, 19k, 19m, submitted for one-dose assay, 19f and 19k were selected for further five-dose testing. Please refer to Supporting Information for more details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.