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CAS No. : | 10212-20-1 | MDL No. : | MFCD00057445 |
Formula : | C9H12FN3O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NVZFZMCNALTPBY-XVFCMESISA-N |
M.W : | 245.21 | Pubchem ID : | 101507 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
100% | In N,N-dimethyl-formamide; at 20℃; | j0950j To a stirred solution of 265-1 (21.0 g, 85.7 mmol) in DMF (100 mL) was added benzoyl anhydride (9.66 g, 87 mmol) in portions. The mixture was stirred at R.T. overnight. The solvent was removed under reduced pressure, and the residue was triturated with CH2C12to give 265-2 as a white solid (29.90 g, 100%). |
100% | In N,N-dimethyl-formamide; at 20℃; | To a stirred solution of compound 12-1 (21.0 g, 85.7 mmol) in DMF (100 mL) was added benzoyl anhydride (9.66 g, 87 mmol) in portions. The mixture was stirred at R.T. overnight. The solvent was removed under reduced pressure, and the residue was triturated with CH2Cl2 to give compound 12-2 as a white solid (29.90 g, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2'-deoxy-2'-fluorocytidine was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-2'-deoxy-2'-fluorocytidine. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites | ||
2'-deoxy-2'-fluorocytidine was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-2'-deoxy-2'-fluorocytidine. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites. | ||
2'-deoxy-2'-fluorocytidine was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-2'-deoxy-2'-fluorocytidine. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites |
'-Fluorodeoxycytidine 2'-deoxy-2'-fluorocytidine was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-2'-deoxy-2'-fluorocytidine. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites. | ||
[0159] 2?-deoxy-2?-fluorocytidine was synthesized via amination of 2?-deoxy-2?-fluorouridine, followed by selective protection to give N4-benzoyl-2?-deoxy-2?-fluorocytidine. Standard procedures were used to obtain the 5?-DMT and 5?-DMT-3?phosphoramidites. | ||
[0157] 2?-deoxy-2?-fluorocytidine was synthesized via amination of 2?-deoxy-2?-fluorouridine, followed by selective protection to give N4-benzoyl-2?-deoxy-2?-fluorocytidine. Standard procedures were used to obtain the 5?-DMT and 5?-DMT-3?phosphoramidites. | ||
2'-deoxy-2'-fluorocytidine was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-2'-deoxy-2'-fluorocytidine. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites. | ||
2'-deoxy-2'-fluorocytidine was synthesized via amination of [2'-DEOXY-2'-] fluorouridine, followed by selective protection to give N4-benzoyl-2'-deoxy-2'- fluorocytidine. Standard procedures were used to obtain the [5'-DMT] and [5'-DMT-] 3'phosphoramidites. | ||
2'-deoxy-2'-fluorocytidine was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-2'-deoxy-2'-fluorocytidine. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites. | ||
2'-deoxy-2'-fluorocytidine was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-2'-deoxy-2'-fluorocytidine. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites. | ||
[[00108]] 2'-deoxy-2'-fluorocytidine is synthesized via amination of [2'-DOXY-] 2'-fluorouridine, followed by selective protection to give [N4-BENZOYL-2'-DEOXY-] [2'-FLUOROCYTIDINE.] Standard procedures are used to obtain the 5'-DMT and [SI-] [DMT-3'PHOSPHORAMIDITES.] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong> was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong>. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites | ||
'-Fluorodeoxycytidine <strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong> was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong>. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites. | ||
<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong> was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong>. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites. |
<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong> was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong>. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites. | ||
<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong> was synthesized via amination of [2'-DEOXY-2'-] fluorouridine, followed by selective protection to give N4-benzoyl-2'-deoxy-2'- fluorocytidine. Standard procedures were used to obtain the [5'-DMT] and [5'-DMT-] 3'phosphoramidites. | ||
<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong> was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong>. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites. | ||
<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong> was synthesized via amination of 2'-deoxy-2'-fluorouridine, followed by selective protection to give N4-benzoyl-<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong>. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites. | ||
[[00108]] <strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong> is synthesized via amination of [2'-DOXY-] 2'-fluorouridine, followed by selective protection to give [N4-BENZOYL-2'-DEOXY-] [2'-FLUOROCYTIDINE.] Standard procedures are used to obtain the 5'-DMT and [SI-] [DMT-3'PHOSPHORAMIDITES.] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine; In N,N-dimethyl-formamide; at 0 - 50℃; for 12.0h; | Synthesis of (2R,3R,4S,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-tetrahydrofuran-3-yl benzoate (2) To a solution of 2-deoxy-2-fluorocytidine (0.32 g, 1.32 mmol) and DMAP (0.32 g, 2.60 mmol) in 5.0 mL of anhydrous DMF was added Et3N (0.27 mL, 1.95 mmol) and TBDPSCl (0.50 mL, 1.96 mmol) at 0 C. under N2 atmosphere. The resulting solution was stirred for 12 h at 50 C. and treated with MeOH (0.5 mL) at rt. After stirring the solution additionally, the solvent was removed under reduced pressure. The residue was dried under high vacuum for 24 h at room temperature. The crude product was dissolved in 10 mL of anhydrous pyridine at 0 C. under N2 atmosphere. To the solution was added to benzoyl chloride (0.4 mL, 3.40 mmol). After stirring the solution at rt for 12 h, the solution was treated with MeOH (1.0 mL) at rt. The solution was concentrated in vacuo and the residue was purified on silica gel column chromatography (Hexane:EtOAc=2:1 to 1:2 v/v) to give compound 2 (0.64 g, 0.92 mmol) in 82% yield. 1H NMR (CDCl3, 400 MHz) delta 9.31 (br, 1H), 8.45 (d, J=8.0, 1H), 7.96 (m, 4H), 7.66-7.37 (m, 15H), 7.18 (m, 2H), 6.26 (d, J=16.0, 1H), 5.50 (m, 1H), 5.48 (d, J=3.5, 0.5H), 5.34 (d, J=3.5, 0.5H), 4.52 (d, J=8.8, 1H), 4.28 (dd, J=12.0, 1.6, 1H), 3.87 (dd, J=12.0, 1.6, 1H), 1.10 (s, 9H); MS calcd for C39H38FN3O6Si m/z 692.3 (M+H)+, found 692.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 70℃; for 3.0h; | A suspension of 12a (24.5 g, 100.0 mmol) in 500 mL of EtOH with acetic anhydride (71.5 g, 700 mmol) was heated to 70 0C. for 3 h. The flask was allowed to cool and the solvents were in vacuo. The resulting oil was coevaporated copiously with absolute EtOH followed by Toluene. The resulting white powder was taken onto the silylation step without any further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; at 20℃; for 18.0h; | 2'-Fluoro-2'-deoxycytidine (223, R=F, 5g) was suspended in anhydrous pyridine (175 mL) and the reaction flask was cooled in an ice bath. To this was added benzoyl chloride (12 mL) and the mixture was stirred at room temperature for 18h. The reaction was quenched by the addition of water (15 ml). After 30 min the reaction mixture was diluted with dichloromethane (300 mL) and washed with saturated sodium bicarbonate solution (2 x 250 mL). Organic layer was dried (sodium sulfate) and evaporated. The residue was co-evaporated with toluene. The solid obtained was suspended in toluene and collected by filtration. The product was dried and used in the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With pyridine; at 20℃; | A solution of <strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong> (20.0 g, 81.6 mmol) and TBDMS-Cl (14.8 g, 97.9 mmol) in anhydrous pyridine (200 mL) was stirred at room temperature overnight and then concentrated. The residue was diluted with ethyl acetate, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 24 g (82%) of 5'-O-(t- butyldimethylsilyl)-<strong>[10212-20-1]2'-deoxy-2'-fluorocytidine</strong> as a white solid. |
With pyridine; at 20℃; for 16.0h;Cooling with ice; | EXAMPLE 1 Preparation of Compound la 102171 To an ice cooled solution of P1-i (10.0 g, 40.8 mmol) in dry pyridine (100 mL) was added TBSC1 in pyridine (1M, 53 mL) dropwise at room temperature (R.T.). The reaction mixture was stirred at R.T. for 16 hours. The reaction mixture was then quenched with water, concentrated to give a residue. The residue was separated by ethyl acetate (EA) and saturated NaHCO3 aq. solution. The organic phase was dried and concentrated. The residue was purified on a silica gel column (5% MeOH in DCM) to give a crude 5?-O-TBS protected intermediate as a white solid (13.4 g, 91%). The intermediate was dissolved in anhydrous DCM (100 mL) and sym-collidine (17.9 g, 149.2 mmol), AgNO3 (25 g, 149.2 mmol) and MMTrCI (45 g, 149.2 mmol) were added. The mixture was stirred at R.T. for 16 hours. The mixture was quenched with water, and the organic layer was separated and concentrated. The residue purified on a silica gel column (30% PE in EA) to give the crude product. The crude product was dissolved in 1M TBAF (50 mL) in THF. The mixture was stirred at R.T. for 2 hours. The solvent was removed, and the residue was purified on a silica gel column (50% PE in EA) to give P1-2 as a white solid (21.4 g, 66% for three steps). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With hydroxylamine hydrochloride; sodium hydroxide; In water; at 55℃; for 16.0h;pH 5.0;Inert atmosphere; | Example 11.EIDD-2085: A ~2 N solution of hydroxylamine hydrochloride (3.33 g, 48.0 mmol) in water (24 mL) was prepared, and adjusted to pH = 5 with a small amount of aq. NaOH (10% w/w). A sealable pressure tube was charged with this solution and <strong>[10212-20-1]2'-fluoro-2'deoxycytidine</strong> (0.736 g, 3.00 mmol), the flask was sealed, and heated with stirring at 55C for 16 h. The mixture was cooled to room temperature, transferred to a round bottom flask, and concentrated by rotary evaporation. The crude material was suspended in MeOH and immobilized on Celite. Automated flash chromatography (40 g column, 5 to 25% gradient of MeOH in DCM) gave the title compound (0.365 g, 47%) as an off-white solid. NMR analysis showed the compound to be -90% pure by weight, with the remainder being occluded DCM and MeOH. A sample (103 mg) was dissolved in water, frozen in a dry ice bath, and lyophilized to give 91 mg of the title compound, solvent-free. This purified material was used for all biological testing: 1H NMR (400 MHz, D20) delta 7.00 (d, J= 8.3 Hz, 1H), 5.91 (dd, J = 21.0 Hz, 2.0 Hz, 1H), 5.71 (d, J= 8.2 Hz, 1H), 5.19 (ddd, J= 53.1 Hz, 5.0 Hz, 2.0 Hz, 1H), 4.36 (ddd, J= 20.0 Hz, 8.2 Hz, 5.0 Hz, 1H), 4.08-4.02 (br m, 1H), 3.95 (dd, J = 12.9 Hz, 2.5 Hz, 1H), 3.78 (dd, J = 12.9 Hz, 4.6 Hz, 1H);13C NMR (100 MHz, D20) delta 150.8, 146.7, 132.5, 98.4, 93.1 (d, J = 183.1 Hz), 89.0 (d, J = 35.9 Hz), 82.1, 68.3 (d, J = 16.5 Hz), 60.2 Hz;19F NMR (376 MHz, D20) delta -200.51 (dt, J = 53.1 Hz, 20.4 Hz); HRMS calcd. for C9H13FN3O5 [M+ H]+: 262.08338, found: 262.08332. |
91 mg | With hydroxylamine hydrochloride; In water; at 55℃; for 16.0h;pH 5.0;Sealed tube; Inert atmosphere; | EIDD-2085: A ~2 N solution of hydroxylamine hydrochloride (3.33 g, 48.0 mmol) in water (24 mL) was prepared, and adjusted to pH = 5 with a small amount of aq. NaOH (10% w/w). A sealable pressure tube was charged with this solution and <strong>[10212-20-1]2'-fluoro-2'deoxycytidine</strong> (0.736 g, 3.00 mmol), the flask was sealed, and heated with stirring at 55C for 16 h. The mixture was cooled to room temperature, transferred to a round bottom flask, and concentrated by rotary evaporation. The crude material was suspended in MeOH and immobilized on Celite. Automated flash chromatography (40 g column, 5 to 25% gradient of MeOH in DCM) gave the title compound (0.365 g, 47%) as an off-white solid. NMR analysis showed the compound to be -90% pure by weight, with the remainder being occluded DCM and MeOH. A sample (103 mg) was dissolved in water, frozen in a dry ice bath, and lyophilized to give 91 mg of the title compound, solvent-free. This purified material was used for all biological testing: 1H NMR (400 MHz, D20) delta 7.00 (d, J= 8.3 Hz, 1H), 5.91 (dd, J = 21.0 Hz, 2.0 Hz, 1H), 5.71 (d, J= 8.2 Hz, 1H), 5.19 (ddd, J= 53.1 Hz, 5.0 Hz, 2.0 Hz, 1H), 4.36 (ddd, J= 20.0 Hz, 8.2 Hz, 5.0 Hz, 1H), 4.08-4.02 (br m, 1H), 3.95 (dd, J = 12.9 Hz, 2.5 Hz, 1H), 3.78 (dd, J = 12.9 Hz, 4.6 Hz, 1H); 13C NMR (100 MHz, D20) delta 150.8, 146.7, 132.5, 98.4, 93.1 (d, J = 183.1 Hz), 89.0 (d, J = 35.9 Hz), 82.1, 68.3 (d, J = 16.5 Hz), 60.2 Hz; 19F NMR (376 MHz, D20) delta -200.51 (dt, J = 53.1 Hz, 20.4 Hz); HRMS calcd. for C9H13FN3O5 [M+ H]+: 262.08338, found: 262.08332. |
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H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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