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Volumn , Issue 3, 2009, Pages 472-476

From intriguing reactivity of 2-bromothiophene to the first synthesis of C1′-disubstituted C-nucleosides

Author keywords

C nucleosides; Cycloetherification; Double aryl aldol condensation

Indexed keywords


EID: 62249154806     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087537     Document Type: Article
Times cited : (9)

References (35)
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    • For pyrazofurin and formycin, see: a, Katritzky, A. R, Ed, Academic Press: San Diego
    • For pyrazofurin and formycin, see: (a) Shaban, M. A. E.; Nasr, A. Z. In Advances in Heterocyclic Chemistry, Vol. 68; Katritzky, A. R., Ed.; Academic Press: San Diego, 1997, 259.
    • (1997) Advances in Heterocyclic Chemistry , vol.68 , pp. 259
    • Shaban, M.A.E.1    Nasr, A.Z.2
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    • For recent articles, see: For a review, see
    • (a) For recent articles, see: For a review, see: Maden, B. E. H. Nature (London) 1997, 389, 129.
    • (1997) Nature (London) , vol.389 , pp. 129
    • Maden, B.E.H.1
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    • For recent reviews on the chemistry of C-glycoside analogues, see: (a) Wu, Q.; Simons, C. Synthesis 2004, 1533.
    • For recent reviews on the chemistry of C-glycoside analogues, see: (a) Wu, Q.; Simons, C. Synthesis 2004, 1533.
  • 29
    • 62249164770 scopus 로고    scopus 로고
    • 2ah: 1H NMR (200 MHz, CDCl3, δ, 1.07-1.11 (2 x s, 9 H, Met-Bu, 1.30 (s, 3 H, Me, 1.48 (s, 3 H, Me, 3.72 (dd, 1 H, J, 3.6, 11.2 Hz, H5′, 3.90 (dd, 1 H, J, 3.5, 11.3 Hz, H5′, 4.36 (t, 1 H, J, 2.5 Hz, H4′, 4.62 (d, 1 H, J, 5.7 Hz, H 3′, 4.75 (s, 1 H, OH, 4.89 (dd, 1 H, J, 1.4, 5.6 Hz, H2′, 6.96 (s, 2 H, H3, H4, 7.37-7.46 (m, 6 H, Ph, 7.57-7.72 (m, 4 H, Ph, 13C NMR (50 MHz, CD 3OD, δ, 19.79 (CMe3, 24.44 (Me, 26.26 (Me, 26.51 (CMe3, 66.35 (C5′, 84.63 (C 2′, 87.19 (C4′ or C3′, 88.07 (C3′ or C4′, 106.85 (CMe2, 113.40 (C1′, 113.80 (C2, 126.15 (C4, 127.60 CPh
    • 5SSi: C, 57.04; H, 5.64. Found: C, 57.17; H, 5.73.
  • 30
    • 62249093517 scopus 로고    scopus 로고
    • 2b: 1H NMR (200 MHz, CDCl3, CD 3OD, δ, 0.95 (s, 9 H, Met-Bu, 1.24 (s, 3 H, Me, 1.36 (s, 3 H, Me, 3.26-3.39 (m, 2 H, H5′, 3.62 (d, 1 H, J, 4.0 Hz, H4′, 4.26 (dd, 1 H, J, 6.8, 9.8 Hz, H 3′, 4.65 (d, 1 H, J, 6.8 Hz, H2′, 6.68 (d, 1 H, J, 3.9 Hz, H4, 6.76 (d, 1 H, J, 3.9 Hz, H3, 6.84 (d, 1 H, J, 3.8 Hz, H3, 7.05 (d, 1 H, J, 3.9 Hz, H4, 7.27-7.36 (m, 6 H, Ph, 7.45-7.62 (m, 4 H, Ph, 13C NMR (50 MHz, CDCl3, CD3OD, δ, 19.65 (CMe3, 24.14 (Me, 26.54 (Me, 27.14 (Me, t-Bu, 65.68 (C4′, 69.58 (C5′, 76.09 (C 3′, 77.63 (C1′, 83.83 (C2′, 109.32 (CMe2, 112.38-113.32 (C2, 125.54-125.60 C 4
    • +.
  • 31
    • 62249096640 scopus 로고    scopus 로고
    • K could be explained by the possible anisotropy of the TBDPS group (aryl-TBDPS π-stacking).
    • K could be explained by the possible anisotropy of the TBDPS group (aryl-TBDPS π-stacking).
  • 32
    • 62249116092 scopus 로고    scopus 로고
    • 4ah: 1H NMR (200 MHz, CDCl3, δ, 1.07-1.12 (2 x s, 9 H, Met-Bu, 1.25 (s, 3 H, Me, 1.38 (s, 3 H, Me, 3.75 (dd, 1 H, J, 3.1, 11.2 Hz, H5′, 3.95 (dd, 1 H, J, 3.0, 11.5 Hz, H5′, 4.42-4.47 (m, 1 H, H 4′, 4.66 (d, 1 H, J, 5.7 Hz, H2′, 4.87-4.95 (m, 2 H, H3′, OH, 7.24-7.26 (m, 1 H, Ar, 7.37-7.71 (m, 13 H, Ph, Ar, 13C NMR (50 MHz, CDCl3, δ, 19.20 (CMe3, 24.87 (Me, 26.37 (Me, 26.92 (CMe3, 65.62 (C5′, 82.04 (C3′, 86.40 (C 4′, 88.36 (C2′, 106.60 (C 1′, 112.87 (CMe2, 121.82 (C3, 124.59 (CHAr, 127.84 (CPh, 129.15 (CHAr, 129.82 (CHAr, 130.19 (CPh, 130.39 (CHAr, 131.22 CPh, 135.62
    • +.
  • 33
    • 62249134859 scopus 로고    scopus 로고
    • 7ah: 1H NMR (200 MHz, CDCl3, δ, 1.08-1.12 (2 x s, 9 H, Met-Bu, 1.26 (s, 3 H, Me, 1.40 (s, 3 H, Me, 3.71-4.01 (m, 5 H, H5′, OMe, 4.38-4.52 (m, 2 H, H 4′, OH, 4.63 (d, 1 H, J, 5.7 Hz, H2′, 4.92 (dd, 1 H, J, 1.5, 5.7 Hz, H3′, 6.89 (d, 2 H, J, 8.9 Hz, H3, 7.36-7.44 (m, 6 H, Ph, 7.54 (d, 2 H, J, 8.8 Hz, H2, 7.65-7.75 (m, 4 H, Ph, 13C NMR (50 MHz, CDCl3, δ, 19.39-19.49 (CMe3, 25.14-25.20 (Me, 26.71-26.82 (Me, 27.04-27.11 (CMe3, 55.38 (OMe, 65.88 (C5′, 82.23-82.33 (C3′, 86.43-86.54 (C 4′, 88.25 (C2′, 107.30 (C 1′, 112.84 (CMe2, 113.12 (C3, 128.08-128.13 (CPh, 128.44 (C2, 130.19-130.35 (C Ph, 131.60 C
    • k.
  • 34
    • 62249104892 scopus 로고    scopus 로고
    • 2c: 1H NMR (200 MHz, CDCl3, δ, 1.05 (s, 9 H, Met-Bu, 1.29 (s, 3 H, Me, 1.39 (s, 3 H, Me, 3.70-4.12 (m, 3 H, H4′, H5′, 4.76 (dd, 1 H, J, 2.9, 5.9 Hz, H3′, 5.01 (d, 1 H, J, 5.8 Hz, H 2′, 6.41 (d, 1 H, J, 3.8 Hz, H4, 6.83 (d, 1 H, J, 3.9 Hz, H3, 6.87 (d, 1 H, J, 3.9 Hz, H 3, 6.98 (d, 1 H, J, 3.8 Hz, H4, 7.32-7.45 (m, 6 H, Ph, 7.65-7.78 (m, 4 H, Ph, 13C NMR (50 MHz, CDCl3, δ, 19.38 (CMe3, 24.68 (Me, 25.77 (Me, 26.94 (CMe 3, 61.83 (C5′, 77.36, 78.88, 80.43, 81.37 (C 4′, C3′, C1′, C 2′, 112.38-113.32 (C2, 113.36 (CMe2, 126.13-126.27 (C4, 127.74-127.81 (CPh, 128.83-129.79 C3, 133
    • 2), 7.58-7.69 (m, 4 H, Ph).
  • 35
    • 62249184931 scopus 로고    scopus 로고
    • 2d: mp 181-182°C. 1H NMR (200 MHz, CDCl3, CD3OD, δ, 3.47 (dd, 1 H, J, 2.8, 9.6 Hz, H 5′, 3.69 (dd, 1 H, J, 2.7, 7.9 Hz, H 5′, 3.82-3.96 (m, 2 H, H3′, H 4′, 4.49 (d, 1 H, J, 2.8 Hz, H2′, 6.54 (d, 1 H, J, 3.9 Hz, HTh, 6.87 (d, 1 H, J, 3.9 Hz, HTh, 7.01-7.08 (m, 2 H, HTh, 13C NMR (50 MHz, CDCl3, CD3OD, δ, 62.47 (C 5′, 71.33 (C3′, 80.42 (C4′, 82.65 (C2′, 88.64 (C1′, 112.09-112.18 (C2, 125.67-126.22 (C4, 128.26-129.30 (C3, 140.58-141.82 (C5, MS (ESI, m/z, 476.5, 478.5, 480.5 49, 100, 54, M, Na, Anal. Calcd for C13H 12Br2O4
    • 6: C, 65.88; H, 6.40. Found: C, 66.03; H, 6.29.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.