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Volumn , Issue 19, 2008, Pages 2993-2996

Design and synthesis of 3′-deoxy-3′-fluoro-2′-O-3′- C-vinylene-linked bicyclic purine nucleoside

Author keywords

Bicyclic nucleoside; Ethynyl group; Fluorine; Intramolecular cyclization; Neighboring group participation

Indexed keywords

CARBOHYDRATE DERIVATIVE; PURINE NUCLEOSIDE DERIVATIVE; XYLOSE;

EID: 57649123157     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1087227     Document Type: Article
Times cited : (7)

References (58)
  • 27
    • 26644452107 scopus 로고    scopus 로고
    • Moukhachafiq, O.; Tiwari, K. N.; Secrist, J. A. III Nucleosides, Nucleotides Nucleic Acids 2005, 24, 713.
    • Moukhachafiq, O.; Tiwari, K. N.; Secrist, J. A. III Nucleosides, Nucleotides Nucleic Acids 2005, 24, 713.
  • 41
    • 57649122865 scopus 로고    scopus 로고
    • Compound 10: space group P212121 with cell parameters: a, 7.4156(15) nm, b, 20.417(4) nm, c, 23.585(5) nm; CCDC 701133
    • Compound 10: space group P212121 with cell parameters: a = 7.4156(15) nm, b = 20.417(4) nm, c = 23.585(5) nm; CCDC 701133.
  • 50
    • 0001120760 scopus 로고    scopus 로고
    • (a) Kool, E. T. Chem. Rev. 1997, 97, 1473.
    • (1997) Chem. Rev , vol.97 , pp. 1473
    • Kool, E.T.1
  • 53
    • 57649128031 scopus 로고    scopus 로고
    • 3): δ = 165.4, 164.1, 139.7, 133.5, 131.3, 129.9, 129.1, 128.7, 128.4, 128.2, 113.6, 104.7, 82.6, 78.1, 77.9, 77.8, 77.2, 63.8, 26.8, 26.6.
    • 3): δ = 165.4, 164.1, 139.7, 133.5, 131.3, 129.9, 129.1, 128.7, 128.4, 128.2, 113.6, 104.7, 82.6, 78.1, 77.9, 77.8, 77.2, 63.8, 26.8, 26.6.
  • 54
    • 57649126977 scopus 로고    scopus 로고
    • 3): δ = 165.7, 165.5, 139.6, 133.8, 131.2, 130.0, 128.8, 128.6, 128.4, 107.1, 83.1, 81.4, 80.0, 77.2, 73.7, 65.2, 56.1.
    • 3): δ = 165.7, 165.5, 139.6, 133.8, 131.2, 130.0, 128.8, 128.6, 128.4, 107.1, 83.1, 81.4, 80.0, 77.2, 73.7, 65.2, 56.1.
  • 55
    • 57649116902 scopus 로고    scopus 로고
    • +]: 455.0674; found: 455.0672.
    • +]: 455.0674; found: 455.0672.
  • 56
    • 57649114305 scopus 로고    scopus 로고
    • 3): δ = -185.7.
    • 3): δ = -185.7.
  • 57
    • 57649127578 scopus 로고    scopus 로고
    • 3): δ = 165.4, 164.2, 162.6, 153.2, 146.7, 142.8, 140.4, 134.7, 131.4, 130.3, 129.1, 128.0, 127.8, 122.0, 93.8, 90.3, 84.0, 83.0, 80.9, 72.7, 60.9.
    • 3): δ = 165.4, 164.2, 162.6, 153.2, 146.7, 142.8, 140.4, 134.7, 131.4, 130.3, 129.1, 128.0, 127.8, 122.0, 93.8, 90.3, 84.0, 83.0, 80.9, 72.7, 60.9.
  • 58
    • 57649133240 scopus 로고    scopus 로고
    • Compound 10: white solid, mp 112-115°C 1H NMR (500 Hz, DMSO-d6, δ, 8.86 (s, 1 H, 8.62 (s, 1 H, 7.03 (t, J, 2.5 Hz, 1 H, 5.95 (d, J, 6.0 Hz, 1 H, 5.68 (dd, J, 6.0, 26.5 Hz, 5.62 (d, J, 2.5 Hz, 1 H, 5.01 (t, J, 5.0 Hz, 1 H, 4.25-4.20 (m, 1 H, 4.06 (s, 3 H, 3.82-3.77 (m, 1 H, 3.71-3.66 (m, 1 H, 13C NMR (75 Hz, DMSO-d6, δ, 162.86, 157.15, 153.48 (d, J, 9.0 Hz, C-2, 152.88, 147.27, 112.07, 111.17 (d, 2JC-F, 202.1 Hz, C-3a, 103.91 (d, 3JC-F, 24.5 Hz, C-3, 91.16 (d, 3JC-F, 25.3 Hz, C-4, 90.63 (d, J, 13.0 Hz, C-6, 86.39 (d, J, 31.3 Hz, C-6a, 60.07 (d, J, 9.0 Hz, CH2OH, 55.60 (OCH3, 19F NMR 400 Hz, DMSO-d6, δ, 167.61. ESI-HRMS: m/z calcd for C13H13
    • +]: 331.0819; found: 331.0811.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.