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CAS No. : | 14470-28-1 | MDL No. : | MFCD00000814 |
Formula : | C20H17ClO | Boiling Point : | No data available |
Linear Structure Formula : | ClC(C6H5)3OCH2 | InChI Key : | OBOHMJWDFPBPKD-UHFFFAOYSA-N |
M.W : | 308.80 | Pubchem ID : | 84462 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | 1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-2-yl]-4-[[(4-methoxyphenyl)-diphenyl-methyl]amino]pyrimidin-2-one (E-5) 2'-C-Methylcytidine (38.9 mmol) was dissolved in pyridine (270 mL) and the reaction mixture was cooled down to 0 C. TMSCl (233.4 mmol) was added and the mixture was stirred at room temperature during 4 hours. DMAP (38.9 mmol) and mMTrCl (77.25 mmol) were added and the reaction mixture was stirred at 50 C. during 2 days. The reaction was cooled down to room temperature and a saturated solution of NaHCO3 was added slowly. The mixture was extracted with CH2Cl2 and the organic layer was dried over Na2SO4, filtered and concentrated. Co-evaporations with toluene and CH2Cl2 were done. The crude was dissolved in CH3OH (500 mL) and NH4F (194.5 mmol) was added. The reaction mixture was heated at reflux and stirred during 1 hour. The reaction mixture was cooled down to room temperature and concentrated. The crude was purified by chromatography on a silica gel column (eluent: CH2Cl2/CH3OH 0 to 10%) to give the expected compound as a yellow powder in 89% yield. 1H NMR (CDCl3, 400 MHz) delta (ppm) 1.08 (s, 3H), 3.71-3.84 (m, 2H), 3.81 (s, 3H), 3.90-3.94 (m, 1H), 3.99-4.03 (m, 1H), 5.14 (d, J=7.63 Hz, 1H), 5.31 (s, 1H), 5.79 (brs, 1H), 6.84 (d, J=8.65 Hz, 2H), 7.13 (d, J=8.69 Hz, 2H), 7.21 (d, J=7.35 Hz, 4H), 7.27-7.34 (m, 8H), 7.51 (brs, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; at 20℃;Inert atmosphere; | Commercial 2?-deoxy-2?-difluorouridine (140mg) was dissolved in dry pyridine (2.5mL) undernitrogen and 4-methoxytrityl chloride (246mg, 1.5 eq.) added to the solution. The resulting mixturewas stirred overnight at rt. LC-MS showed complete conversion into the 5?-MMTr protected intermediate. To the mixture was then added acetic anhydride (60L, 1.2 eq.) and the reaction stirredat rt for 2h. LC-MS showed complete conversion into the 5?-MMTr-3?-Ac protected intermediate andthe mixture was quenched by addition of methanol. Solvents were removed by evaporation and theresidue partionated between DCM (10mL) and saturated sodium bicarbonate solution (10mL). Thephases were separated and the water layer extracted with DCM (2x10mL). The combined organiclayers were dried over sodium sulphate, filtered and concentrated to dryness. The crude residue wastaken into 80% acetic acid (30mL) and heated at 45C for 5h. The solution was then concentrated todryness and the residue purified by chromatography on silica gel using DCM/EtOH: 100/0, 98/2, 96/4to yield the desired (2R,3R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl acetate (68mg, 42%). |