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Volumn 5, Issue 18, 2003, Pages 3269-3272

General access to iminosugar C-glycoside building blocks by means of cross-metathesis: A gateway to glycoconjugate mimetics

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYNOJIRIMYCIN DERIVATIVE; GLYCOSIDE;

EID: 0141744688     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035117h     Document Type: Article
Times cited : (60)

References (33)
  • 7
    • 0141804127 scopus 로고    scopus 로고
    • Iminosugars: Recent insights into their bioactivity and potential as therapeutic agents
    • Bentham: Hilversum, The Netherlands
    • Iminosugars: Recent Insights Into Their Bioactivity and Potential As Therapeutic Agents. In Current Topics in Medicinal Chemistry; Martin, O. R., Compain, P., Eds.; Bentham: Hilversum, The Netherlands, 2003; Vol. 3, Issue 5.
    • (2003) Current Topics in Medicinal Chemistry , vol.3 , Issue.5
    • Martin, O.R.1    Compain, P.2
  • 15
    • 0033597743 scopus 로고    scopus 로고
    • See for example: (a) Roy, R.; Dominique, R.; Das, S. J. Org. Chem. 1999, 64, 5408. (b) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58. (c) Plettenburg, O.; Mui, C.; Bodmer-Narkevitch, V.; Wong, C.-H. Adv. Synth. Catal. 2002, 344, 622. (d) Dondoni, A.; Giovanni, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2001, 2380. (e) Biswas, K.; Coltart, D. N.; Danishefsky, S. J. Tetrahedron Lett. 2002, 43, 6107.
    • (1999) J. Org. Chem. , vol.64 , pp. 5408
    • Roy, R.1    Dominique, R.2    Das, S.3
  • 16
    • 0034639441 scopus 로고    scopus 로고
    • See for example: (a) Roy, R.; Dominique, R.; Das, S. J. Org. Chem. 1999, 64, 5408. (b) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58. (c) Plettenburg, O.; Mui, C.; Bodmer-Narkevitch, V.; Wong, C.-H. Adv. Synth. Catal. 2002, 344, 622. (d) Dondoni, A.; Giovanni, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2001, 2380. (e) Biswas, K.; Coltart, D. N.; Danishefsky, S. J. Tetrahedron Lett. 2002, 43, 6107.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 58
    • Blackwell, H.E.1    O'Leary, D.J.2    Chatterjee, A.K.3    Washenfelder, R.A.4    Bussmann, D.A.5    Grubbs, R.H.6
  • 17
    • 0141469359 scopus 로고    scopus 로고
    • See for example: (a) Roy, R.; Dominique, R.; Das, S. J. Org. Chem. 1999, 64, 5408. (b) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58. (c) Plettenburg, O.; Mui, C.; Bodmer-Narkevitch, V.; Wong, C.-H. Adv. Synth. Catal. 2002, 344, 622. (d) Dondoni, A.; Giovanni, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2001, 2380. (e) Biswas, K.; Coltart, D. N.; Danishefsky, S. J. Tetrahedron Lett. 2002, 43, 6107.
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 622
    • Plettenburg, O.1    Mui, C.2    Bodmer-Narkevitch, V.3    Wong, C.-H.4
  • 18
    • 0034740840 scopus 로고    scopus 로고
    • See for example: (a) Roy, R.; Dominique, R.; Das, S. J. Org. Chem. 1999, 64, 5408. (b) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58. (c) Plettenburg, O.; Mui, C.; Bodmer-Narkevitch, V.; Wong, C.-H. Adv. Synth. Catal. 2002, 344, 622. (d) Dondoni, A.; Giovanni, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2001, 2380. (e) Biswas, K.; Coltart, D. N.; Danishefsky, S. J. Tetrahedron Lett. 2002, 43, 6107.
    • (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 2380
    • Dondoni, A.1    Giovanni, P.P.2    Marra, A.3
  • 19
    • 0037179181 scopus 로고    scopus 로고
    • See for example: (a) Roy, R.; Dominique, R.; Das, S. J. Org. Chem. 1999, 64, 5408. (b) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58. (c) Plettenburg, O.; Mui, C.; Bodmer-Narkevitch, V.; Wong, C.-H. Adv. Synth. Catal. 2002, 344, 622. (d) Dondoni, A.; Giovanni, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2001, 2380. (e) Biswas, K.; Coltart, D. N.; Danishefsky, S. J. Tetrahedron Lett. 2002, 43, 6107.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 6107
    • Biswas, K.1    Coltart, D.N.2    Danishefsky, S.J.3
  • 22
    • 0141580998 scopus 로고    scopus 로고
    • note
    • In our case, N-allyl or N-PMB groups were found to be partially or totally cleaved during the deprotection of the acetal function in aqueous TFA.
  • 33
    • 0037450989 scopus 로고    scopus 로고
    • For related examples with 1-C-vinyl glycoside, see: (a) Roy, R.; Das, S. K.; Dominique, R.; Trono, M. C.; Hernandez-Mateo, F.; Santoyo-Gonzalez, F. Pure Appl. Chem. 1999, 71, 565. (b) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2449
    • Nolen, E.G.1    Kurish, A.J.2    Wong, K.A.3    Orlando, M.D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.