Synthesis of carbon E, e -diene chain-linked dinucleotide analogues

Synlett

Volumn , Issue 20, 2009, Pages 3341-3345

  Fargeas, Valérie ^a   Ané, Adjou ^b   Dubreuil, Didier ^a   Lebreton, Jacques ^a  

^a UNIVERSITÉ DE NANTES   (France)

^b UNIVERSITÉ FÉLIX HOUPHOUËT BOIGNY   (Côte d’Ivoire)

Author keywords

Alkynes; Antisense agents; Isomerizations; Nucleobases; Stille reactions

Indexed keywords

ALKADIENE; CARBON; DIMER; DINUCLEOTIDE; THYMIDINE DERIVATIVE; TIN DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; ISOMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 72149111662     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218357     Document Type: Article

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33. Selected Physicochemical Data for Compound 7 1H NMR (400 MHz, CDCl3): d = 1.99 (s, 9 H, t-Bu), 1.82 1.92 (m, 1 H, H2), 1.89 (s, 3 H, CH3), 2.39 (ddd, 1 H, J = 10.0, 6.5, 3.0 Hz, H2), 4.20 (ddd, 1 H, J = 10.0, 3.0 Hz, H3), 4.24 (m, 1 H, H4), 6.23 (br s, 2 H, H5 and H6), 6.34 (dd, 1 H, J = 6.5 Hz, H1), 6.93 (d, 1 H, J = 1.0 Hz, H6), 7.387.50 (m, 6 H, Har), 7.597.67 (m, 4 H, Har), 9.28 (br s, 1 H, NH) ppm. 13C NMR (100 MHz, CDCl3): d = 12.6 (CH3, CH3), 18.9 (C, t-Bu), 26.8 (CH3, t-Bu), 39.6 (CH, C2), 75.4 (CH, C3), 80.7 (CH, C6), 84.8 (CH, C1), 88.2 (CH, C4), 111.3 (C, C5), 127.9, 128.0 (CH, Car), 130.2 (CH, Car), 132.7 (C, Car), 134.9 (CH, C6), 135.6, 135.8 (CH, Car), 142.1 (CH, C5), 150.2 (C, C=O), 163.6 (C, C=O) ppm. MS (CI/NH3): m/z (C27H31I N2O4Si) = 620 [M + NH4 +], 603 [M + H+].
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43. For an interesting discussion on C-3 radical allylation on thymidine, see: (d) Horton, D.; Chen, K.; No, Z.; Lee, H. C. Carbohydr. Res. 2007, 342, 259.
44. Selected Physicochemical Data for Compound 6 1H NMR (400 MHz, CDCl3): d = 0.700.80 (15 H, 3 CH3 and 3 CH2, CH3 and CH2 n-Bu), 1.02 (s, 9 H, 3 CH3, t-Bu), 1.101.27 (m, 6 H, 3 CH2, n-Bu), 1.38 (m, 6 H, 3 CH2, n-Bu), 2.26 (m, 1 H, H2), 2.40 (m, 1 H, H2), 2.40 (s, 3 H, CH3), 3.14 (m, 1 H, H3), 3.753.86 (m, 2 H, H4 and H5), 4.11 (m, 1 H, H5), 5.76 (dd, 1 H, J = 7.0, 19.0 Hz, H3), 6.15 (d, 1 H, J = 19.0 Hz, H3), 6.16 (dd, 1 H, J = 3.0, 7.0 Hz, H1), 7.22 7.49 (m, 6 H, Har), 7.66 (s, 1 H, H6), 7.627.84 (m, 4 H, Har), 9.50 (s, 1 H, NH) ppm. 13C NMR (100 MHz, CDCl3): d = 9.4 (CH2, n-Bu), 11.9 (CH3, CH3), 13.6 (CH3, n-Bu), 19.4 (C, t- Bu), 27.1 (CH3, t-Bu), 27.4 (CH2, n-Bu), 29.0 (CH2, n-Bu), 39.3 (CH2, C2), 45.0 (CH, C3), 62.5 (CH2, C5), 84.7 (CH, C1), 85.6 (CH, C4), 110.5 (C, C5), 127.8 (CH, Car), 129.8 (CH, Car), 132.5 (CH, C3), 132.8, 133.3 (C, Car), 135.2, 135.4 (CH, Car), 135.6 (CH, C6), 145.5 (CH, C3), 150.5 (C=O), 164.2 (C=O) ppm. ESI-HRMS: m/z [M + H+] calcd for C40H61N2O4SiSn [M(119Sn) + H]+: 780.3433; found:
45. For a general review, see:, Espinet P, Echavarren A M., Angew. Chem. Int. Ed. 2004 43 4704; and references cited therein
46. (s, 1 H, H6A), 7.757.56 (m, 8 H, Har), 8.878.80 (2 br s, 2 H, 2 NH) ppm. 13C NMR (100 MHz, CDCl3): d = 12.1 (CH3, CH3A), 12.3 (CH3, CH3B), 19.0 (C, t-Bu), 19.4 (C, t-Bu), 26.8 (CH3, t-Bu), 27.0 (CH3, t-Bu), 39.4 (CH2, C2A), 40.0 (CH2, C2B), 40.7 (CH, C3A), 62. 8 (CH2, C5A), 76.5 (CH, C4B), 84.8 (CH, C1A), 85.1 (CH, C1B), 85.6 (CH, C3B), 86.8 (CH, C4A), 110.7 (C, C5A or C5B), 111.1 (C, C5A or C5B), 128.0 (CH, CHar), 129.2 (CH, Cd), 130.1 (CH, CHar), 131.5 (CH,Cb and Cc), 132.3 (C, Car), 132.6 (CH, Ca), 133.2 (C, Car), 135.4, 135.5, 135.8, 135.9 (CH, CHar, C6A and C6B), 150.3 (C, C=O), 163.6 (C, C=O) ppm. The letter A refers to the upper moiety of the dimer 8. ESI-HRMS: m/z [M + Na+] calcd for C55H64N4O8Si2Na: 987.4160; found: 987.4162.
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50. Selected Physicochemical Data for Compound 20 1H NMR (400 MHz, CDCl3): d = 1.10 (s, 9 H, t-Bu), 1.11 (s, 9 H, t-Bu), 1.62 (s, 3 H, CH3A), 1.84 (s, 3 H, CH3B), 1.87 2.08 (ddd, 1 H, J = 5.0, 9.0, 14.0 Hz, H2B), 2.322.66 (m, 3 H, H2A and H2B), 3.42 (ddd, 1 H, J = 8.0, 8.0, 8.0 Hz, H3A), 3.83 (dd, part A of an AB system, 1 H, J = 2.0, 12.0 Hz, H5A), 4.00 (ddd, 1 H, J = 2.0, 7.0, 12.0 Hz, H4A), 4.08 (dd, part B of an AB system, 1 H, J = 2.0, 12.0 Hz, H5A), 4.53 (d, 1 H, J = 4.0 Hz, H3B), 4.67 (s, 1 H, H4B), 6.20 (dd, 1 H, J = 13.0, 6.0 Hz, H1A), 6.57 (dd, 1 H, J = 6.0, 8.0 Hz, H1B), 7.347.51 (m, 14 H, Har, H6A and H6B), 7.627.68 (m, 8 H, Har), 9.16 (br s, 1 H, NH), 9.30 (br s, 1 H, NH) ppm. 13C NMR (100 MHz, CDCl3): d = 12.1 (CH3, CH3A), 12.7 (CH3, CH3B, 19.0 (C, t-Bu), 19.4 (C, t-Bu), 26.8 (CH3, t-Bu), 26.9(CH3, t-Bu), 29.6 (CH, C3A), 38.9 (CH2, C2A), 40.5 (CH2, C2B), 62.5 (CH2, C5A), 66.4, 72.9, 73.5, 80.0 (C, Ca, Cb, Cc and Cd), 71.9 (CH, C4B), 73.2 (CH, C3B), 84.6 (CH, C1A), 84.9 (CH, C4A), 86.7 (CH, C1B), 111.3 (C5A and C5B), 127.9, 128.0 (CH, CHar), 130.1 (CH, C6A or C6B), 130.2 (CH, C6A or C6B), 132.5, 132.6 (C, Car,), 134.9 (CH, CHar), 135.3, 135.5, 135.6 (CH, CHar), 150.4 (C, C=O), 163.7 (C, C=O) ppm. The letter A refers to the upper moiety of the dimer 20. ESIHRMS: m/z [M + Na+] calcd for C55H60N4O8Si2Na: 983.3847; found: 983.3837.
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