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For dielhynylnaphthalene, biphenylene, and antracene-tethered pyrimidine bases, see
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Synthesis of 5′-protected (acetyl or tert-butyldimethylsilyl) derivatives of 3 by the reaction of adequately protected 5-iodouridine with bis(tributylstannyl)acetylene has been reported in ref. [5]. For synthesis of the 4,4′-dimethoxytrityl derivative of 3, see ref. [6a].
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Synthesis of 5′-protected (acetyl or tert-butyldimethylsilyl) derivatives of 3 by the reaction of adequately protected 5-iodouridine with bis(tributylstannyl)acetylene has been reported in ref. [5]. For synthesis of the 4,4′-dimethoxytrityl derivative of 3, see ref. [6a].
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45
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84869575751
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[6b]
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[6b]
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46
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33344476783
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Biological activity but no synthesis or characterization for 5 has been reported, see: a V. L. Andronova. A. A. Pchelintseva, A. V. Ustinov, A. L. Petrunina, V. A. Korshun. M. V. Skorobogatyi, G. A. Galegov, Voprosy Virusologii 2006, 51, 34-38;
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50
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67949122263
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For examples of comparative studies of communication with the use of these fragments in organometallic systems, see reference [14 f
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For examples of comparative studies of communication with the use of these fragments in organometallic systems, see reference [14 f].
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51
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33747152824
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Representative review of antiviral activity of furopyrimidines: C. McGuigan. J. Balzarini. Antiviral Res. 2006, 71, 149-153.
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Representative review of antiviral activity of furopyrimidines: C. McGuigan. J. Balzarini. Antiviral Res. 2006, 71, 149-153.
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56
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67949120718
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Calculated by Spartan/PM3.
-
Calculated by Spartan/PM3.
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-
-
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57
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-
84869575749
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-
4.047(12)-4.078(12) Å as determined by X-ray structure of 3b: for detailed values see the Supporting Information.
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4.047(12)-4.078(12) Å as determined by X-ray structure of 3b: for detailed values see the Supporting Information.
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59
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0141905740
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Numbering according to furo[2,3-d]pyrimidine-2(3H)-one nomenclature. Characterization of bis(furopyrimidine) base has been reported: E. Coutouli-Argyropoulou, M. Tsitabani. G. Petrantonakis, A. Terzis, C. Raptopoulou. Org. Biomol. Chem. 2003, 1382-1388.
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Numbering according to furo[2,3-d]pyrimidine-2(3H)-one nomenclature. Characterization of bis(furopyrimidine) base has been reported: E. Coutouli-Argyropoulou, M. Tsitabani. G. Petrantonakis, A. Terzis, C. Raptopoulou. Org. Biomol. Chem. 2003, 1382-1388.
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67
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67949103972
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The comparison of 1H and 13CNMR signals for 5- alkynyl-2′-deoxyuridines is summarized in the Supporting Information of ref
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13CNMR signals for 5- alkynyl-2′-deoxyuridines is summarized in the Supporting Information of ref. [16].
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2O/DMSO 1:1, 22°C) were: 4, 369/435; 5, 364/ 409:7, 397/456; 8, 370/445.
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2O/DMSO 1:1, 22°C) were: 4, 369/435; 5, 364/ 409:7, 397/456; 8, 370/445.
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2 = 3.8) over the two-exponential fit.
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Efforts to dissolve a sufficient amount of 5 in the EPR matrix were unsuccessful.
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Chemical shifts for Cl′ and C4′ were assigned based on coupling constants. We attributed larger J(C.H) values of those close signals (168.1-178.4Hz vs. 145.1-153.2 Hz) to Cl′. HETCOR spectra for analogous compounds support this assignment, see: A. Sniady, A. Durham, M. S. Morreale. A. Marcinek. S. Szafert, T. Lis. K. R. Brzezinska. T. Iwasaki. T. Ohshima. K. Mashima. R. Dembinski, J. Org. Chem. 2008, 73, 5881-5889.
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Chemical shifts for Cl′ and C4′ were assigned based on coupling constants. We attributed larger J(C.H) values of those close signals (168.1-178.4Hz vs. 145.1-153.2 Hz) to Cl′. HETCOR spectra for analogous compounds support this assignment, see: A. Sniady, A. Durham, M. S. Morreale. A. Marcinek. S. Szafert, T. Lis. K. R. Brzezinska. T. Iwasaki. T. Ohshima. K. Mashima. R. Dembinski, J. Org. Chem. 2008, 73, 5881-5889.
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The C2′ signal was obscured by the solvent resonance.
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67949091515
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Although 13C-1H-coupled NMR (gated decoupling) spectra were acquired, we were not able unambiguously assign all J. values and signals. Due to repeated atom numbers in both nucleoside components, labeling from the X-ray structure was used for signal assignments
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1H-coupled NMR (gated decoupling) spectra were acquired, we were not able unambiguously assign all J. values and signals. Due to repeated atom numbers in both nucleoside components, labeling from the X-ray structure was used for signal assignments.
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