C(5)); 68.43 (C(three)); 70.09 (C(1); 83.16 (C(2); 87.27 (C(four)); 87.73 (C(1)); 102.27 (C(5)); 113.47 (C(ar)); 127.33 (C(ar)); 130.25 (C(ar));140.32 (C(six)); 144.50; 150.33; 158.91; 163.39 ppm. ESI-MS (m/z): [M+Na]+ calcd for C32H33N5O8Na, 638.21; found 638.forty. 2-O-(2-Azidoethyl)-5-O-(four,4-dimethoxytrityl)-3-O[1,6-dioxo-6-(pentafluorophenyloxy)hexyl]uridine (2b). Compound 2a (one hundred mg, 162 mol) was coevaporated with pyridine twice and dried above P2O5 for 3 hours, then it had been dissolved in DMF/Pyr (=1/1; four.six mL) and DMAP (24 mg, 196 mol), and adipinic acid pentafluorophenyl ester (275 mg, 575 mol) was additional. After one particular hour the reaction mixture was evaporated and coevaporated with acetone and CH2Cl2 twoArticletimes. The crude solution was purified by column chromatography on SiO2 with acetone/CH2Cl2, 95:five to 85:15. Yield: 70 mg of 2b as a white foam (47 ). TLC (acetone/CH2Cl2 = eight:2): Rf = 0.56. 1H NMR: (300 MHz, CDCl3): 1.93 (m, 4H, RO2CH2(CH2)2CH2-CO2C6F5); 2.58 (m, 2H, RO two CH 2 (CH two ) two CH 2 CO two C six F 5 ); 2.84 (t, J = six.8, 2H, RO2CH2(CH2)2CH2CO2C6F5); three.51 (m, 2H, H1-C(2), H2-C(2)); three.58 (m, 1H; H1-C(five)); three.Buy1-Methylcyclobutanecarboxylic acid 81 (m, 1H, H2- C(5)); 3.86 (m, 1H, H2-C(one)); three.93 (s, 6H, H3CO); 4.11 (m, 1H, H1-C(one)); four.43 (m, 2H, H-C(four)); five.34 (dd, J1 = seven.0, J2 = five.three, 1H, H-C(three)); five.51 (d, J = 8.one Hz, 1H, H-C(five)); 5.93 (d, J = two.55 Hz, 1H, H-C(1), 7.00 (m, 4H, H-C(ar)); 7.forty (m, 9H, H-C(ar)); 8.14 (d, J = eight.1 Hz, 1H, H-C(6)); 9.38 (s, 1H, N-H) ppm. 13C NMR (150 MHz, CDCl3): 24.01, 24.twenty, 33.00, 33.44 (4C, RO 2 CH two (CH two ) 2 CH 2 – CO two C6 F five ), 50.91 (C(two)); 55.39 (2C, CH3 O); 61.18 (C(five)); 69.89 (C(3)); 70.14 (C(one); 80.90 (C(four)); 81.23 (C(two); 87.56 (C(1)); 102.60 (C(five)); 113.49 (C(ar)); 127.40 (C(ar)); 130.31 (C(ar)); 135.05; 139.87 (C(six)); 144.24; 150.42; 158.95; 163.32; 169.sixteen; 172.40 ppm. ESI-MS (m/z): [M+Na]+ calcd for C44H40N5F5O11Na, 932.24; discovered 932.32. 2-O-(2-Azidoethyl)Uridine Modified Sound Support (3).Formula of TCEP (hydrochloride) Compound 2b (70 mg, 77 mol) was dissolved in DMF (one.PMID:24025603 seven mL) and pyridine (twelve mg [12 L], 154 mol). Then, amino-functionalized reliable support (GE Healthcare, Customized Primer Assistance 200 Amino, 323 mg) was additional. The suspension was agitated for 48 h at room temperature as well as beads were collected on a Buchner funnel. The beads have been washed with N,N-dimethylformamide, methanol, and dichloromethane and dried. Capping was carried out by remedy with the beads with a mixture of three.0 mL of option A (acetic anhydride/ two,four,6-trimethylpyridine/acetonitrile, 2/3/5) and 3.0 mL of answer B (4-(N,N-dimethylamino)pyridine/acetonitrile, 0.five M) for 5 min at area temperature. The suspension was filtrated once again and also the beads had been washed extensively with acetonitrile, methanol, and dichloromethane and dried underneath vacuum. Loading from the assistance 3 was 60 mol/g. 2-O-([N-Trifluoracetyl]-2-aminoethyl)-5-O-(4,4dimethoxytrityl)uridine (4). Compound 2a (460 mg, 0.75 mmol) was dissolved in THF (seven.25 mL). Water (69 L, 3.8 mmol) and triphenylphosphine (392 mg, 1.five mmol) was extra and also the resolution was stirred for five h at room temperature. Then, ethyl trifluoroacetate (1065 mg [0.89 mL], 7.five mmol) and triethylamine (770 mg [1.06 mL], seven.6 mmol) have been additional and stirring was continued overnight. The reaction mixture was evaporated as well as the crude merchandise was purified by column chromatography on SiO2 with CH2Cl2/CH3OH, one hundred:0 to 95:5. Yield: 315 mg of four as being a white foam (= 61 ). TLC (CH2Cl2/ CH3OH = 95/5): Rf = 0.four. 1H NMR (300 MHz, CDCl3): two.85 (d, J =8.7 Hz, 1H, HO-C(3)); three.50-3.65 (m, 4H, H1.