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With sodium methylate; In methanol; at 20 - 30℃; for 4.0h;
At room temperature, 11.5 g of compound 5 was added to 80 ml of methanol, and 3.3 g of sodium methoxide was added with stirring. The reaction was stirred at 20-30 C for 4 hours. After completion of the reaction, 4.2 g of strongly acidic cationic resin was added and stirred for 30 min. , The filtrate was concentrated and dried. After adding 120 ml of acetone, the mixture was stirred and filtered. The filtrate was concentrated and dried. After the residue was added 60 ml of ethanol and acetoneThe solvent was filtered off and the filtrate was dried at 60 C for 6 h to give 4.9 g of a white solid, yield 82.5%, and HPLC: 99.5%
5-Trifluoromethyl-5'-dimethoxytrityl-2'-deoxyuridine To a stirred solution of 250 mg of 5-trifluoromethyl-2' deoxyuridine (5-Tf-dU) in 20 mL of dry pyridine at 0 C. was added 227 mg of dimethoxytrityl chloride (DMT-Cl) and 10 mg of 4-dimethylaminopyridine (DMAP). The reaction was stirred for 5 hours at room temperature when a second portion of 144 mg of DMT-Cl was added. After stirring for 12 hours at room temperature, a third portion of 100 mg of DMT-Cl was added to the reaction. The reaction was stirred for an additional 4 hours at room temperature and then diluted with CH2Cl2, washed with water and dried over sodium sulfate (Na2SO4). The crude product was purified by silica gel column chromatography (0-10% methanol (MeOH) in CH2Cl2). 485 mg of the desired product (5'-DMT-5-Tf-dU) was obtained as a yellow foam (96% yield).
72%
With pyridine; at 20℃; for 41.5h;Inert atmosphere;
To a solution of compound 2 (70 mg, 0.24 mmol) in pyridine, DMTrCl (96 mg, 0.28 mmol) was added at room temperature under Ar atmosphere. After being stirred for 41.5 h, the reaction was quenched with MeOH and then concentrated in vacuo. The crude residue was purified by column chromatography (CHCl3-MeOH=100 : 1) to give compound 3 as a white solid (101 mg, 72%). The NMR spectral data were identical to those reported in the literature. 24)
With pyrimidine nucleoside phosphorylase from Mycoplasma hyorhinis; In aq. phosphate buffer; at 37℃; for 0.333333h;pH 7.6;Enzymatic reaction;Kinetics;
General procedure: PyNPHyor was cloned and expressed in E. coli BL21 (DE3) pLysS as a glutathione S-transferase fusion protein according to Vande Voorde et al. [10] The conversion of pyrimidine nucleosides to nucleobases was assayed at varying concentrations of substrate after 20 min incubation at 37 C in a reaction mixture containing 9 nM enzyme in TP buffer (pH 7.6; 10 mM Tris-HCl,; 1 mM EDTA; 150 mM NaCl and 200 mM potassium phosphate). After incubation, samples were prepared and analyzed by HPLC analysis using a reverse-phase RP-8 column as described earlier.[10] Lineweaver-Burk plots were performed and the Michaelis constant (Km) and turnover number (kcat) were estimated by linear regression analysis. By simultaneous incubation of nucleosides and nucleobases, PyNPHyor catalyzed (2-deoxy)ribosyltransferase activity was also studied. Paired substrates[thymidine and uracil; 2-deoxyuridine and thymine; uridine and thymine] were exposed to PyNPHyor (9 nM) in TP buffer containing 2 mM Pi. At several time points (0, 20, 40, and 60 min), aliquots were removed and nucleosides and nucleobases were separated using HPLC analysis and quantified according to appropriate standard solutions.
Yield
Reaction Conditions
Operation in experiment
By following the procedure of part A and substituting for thymidine with the following: ... 2'-deoxyuridine, 2'-deoxycytidine, uridine, 9-(2-deoxy-beta-D-erythro-pentofuranosyl)2,6-diaminopurine, 1-(2-deoxy-beta-D-erythro-pentofuranosyl)5-trifluoromethyl-2,4-dioxopyrimidine, 9-(2-deoxy-beta-D-erythro-pentofuranosyl)2-aminopurine, 1-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-fluoro-2,4-dioxopyrimidine, 1-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-chloro-2,4-dioxopyrimidine, ...
The process of claim 1, wherein R2 is selected from the group consisting of: ... 2',3'-dideoxy-2',3'-didehydrocytidine 3'-deoxy-2',3'didehydrothymidine 3'-deoxy-3'azidothymidine 5-fluorouridine 5-trifluoromethyl-2'-deoxyuridine 6-mercaptopurine-9-beta-D-ribofuranoside 2- fluoroadenine-9-beta-D-arabinofuranoside 2-chloro-2'-deoxyadenosine
5-Trifluoromethyl-2'-deoxyuridine CPG To a solution of 400 mg of 5-trifluoromethyl-4'-(3-carboxypropionyl)-5'-di-methoxytrityl-2'-deoxyuridine in 20 mL of dimethylformamide (DMF) was added 98 mg of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU), 135 muL of diisopropylethyl amine (DIPEA) and 7 g of CPG (37 muM/g). The mixture was shaken for 16 hours and then washed with DMF (3*50 mL), THF (3*30 mL) acetonitrile, CH3CN, (2*30 mL) and CH2Cl2 (2*30 mL). The 5-trifluoromethyl-2'-deoxyuridine CPG product was dried under high vacuum for 4 hours.
1-[4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-5-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-trifluoromethyl-1<i>H</i>-pyrimidine-2,4-dione[ No CAS ]
1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-tetrahydro-furan-2-yl}-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester[ No CAS ]
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