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CAS No. : | 22423-26-3 | MDL No. : | MFCD00233555 |
Formula : | C10H12N2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WLLOAUCNUMYOQI-JAGXHNFQSA-N |
M.W : | 240.21 | Pubchem ID : | 168045 |
Synonyms : |
2,2'-Anhydro-5-methyluridine
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.6 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 54.82 |
TPSA : | 93.81 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -9.24 cm/s |
Log Po/w (iLOGP) : | 1.16 |
Log Po/w (XLOGP3) : | -2.08 |
Log Po/w (WLOGP) : | -1.76 |
Log Po/w (MLOGP) : | -0.79 |
Log Po/w (SILICOS-IT) : | -0.78 |
Consensus Log Po/w : | -0.85 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.21 |
Solubility : | 147.0 mg/ml ; 0.611 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.64 |
Solubility : | 1040.0 mg/ml ; 4.34 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.04 |
Solubility : | 217.0 mg/ml ; 0.904 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 4.07 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
95.6% | With sodium hydroxide; Diethyl carbonate In N,N-dimethyl-formamide at 120℃; for 8 h; | The reaction flask was charged with DMF 100 mL, 5-methyluridine (50.0 g, 0.19 mol), sodium hydroxide (0.18 g,4.4mmo 1) and diethyl carbonate (46mL, 0.38mo 1), heated to 120 ° C, the reaction was incubated for 8 hours. After the reaction of TLC detection material was completed, the temperature was lowered to room temperature, the pH was adjusted to neutral (about 7.0) with 30percent hydrochloric acid in ethanol and concentrated to dryness. The concentrate was added with 50 mL of ethyl acetate and refluxed for 1 hour, cooled to room temperature, filtered and the solid was collected. The solid was dried under vacuum at 60 ° C to give the title compound (white solid, 44.5 g) in a molar yield of 95.6percent and HPLC purity of 98.29.percent |
90% | With bis(phenyl) carbonate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; | The scheme below shows the synthesis of the 2′-DIBO-5-methyluridine phosphoramidite compound B: (i) diphenyl carbonate, NaHCO3 cat., 100° C., DMF, 90percent, (ii) DMTCl, pyridine, rt, 89percent, (iii) ethylene glycol, Ti(OiPr)4, NaHCO3 cat., THF, 150° C., 79percent, (iv) MsCl, Et3N, DCM, 57percent, (v) NaN3, DMF, 18-crown-6, 89percent, (vi) Ph3P, H2O, THF, 89percent (vii) DCM, Et3N, 88percent, (viii) (iPr)2NP(Cl)OCH2CH2CN, DIPEA, DCM, rt, 59.4percent. |
85% | With bis(phenyl) carbonate; sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide) for 1 h; Heating / reflux | 5-Methyluridine (ribosylthymine, commercially available through Yamasa, Choshi, Japan) (72.0 g, 0.279 M), diphenylcarbonate (90.0 g, 0.420 M) and sodium bicarbonate (2.0 g, 0.024 M) were added to DMF (300 mL). The mixture was heated to reflux, with stirring, allowing the evolved carbon dioxide gas to be released in a controlled manner. After 1 hour, the slightly darkened solution was concentrated under reduced pressure. The resulting syrup was poured into diethylether (2.5 L), with stirring. The product formed a gum. The ether was decanted and the residue was dissolved in a minimum amount of methanol (ca. 400 mL). The solution was poured into fresh ether (2.5 L) to yield a stiff gum. The ether was decanted and the gum was dried in a vacuum oven (60° C. at 1 mm Hg for 24 h) to give a solid that was crushed to a light tan powder (57 g, 85percent crude yield). The NMR spectrum was consistent with the structure, contaminated with phenol as its sodium salt (ca. 5percent). The material was used as is for further reactions (or it can be purified further by column chromatography using a gradient of methanol in ethyl acetate (10-25percent) to give a white solid, mp 222-4° C.). |
78% | With sodium hydrogencarbonate; carbonic acid dimethyl ester In N,N-dimethyl-formamide at 130℃; for 2 h; | 5-methyluridine (3) (15 g, 58.06 mmol) was dissolvedin dry dimethylformamide (100 mL) and treated with dimetyl carbonate (6.95 mL, 81.87 mmol) and sodium hydrogen carbonate (0.31 g, 3.71 mmol). The mixture was heated at 130 °C for 2 h and poured into ether. The precipitated gum was then crystallized from methanol to give the 2,2’-anhydrothymidine (4) as colorless prisms (10.9 g, 78percent); [α]D20,5 –0.09 (c = 0.4, MeOH); mp 240-242 °C; IR ν/cm-1 3070, 2890, 1666, 1550, 1480, 1240,1060, 990, 790. |
47% | With bis(phenyl) carbonate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 150℃; | See: J. Med. Chem. 1979, 22, 1273-1277. To a round bottom flask containing 21 (10 g, 38.6 mmol) in DMF 20 mL, was added (PhO)2CO (12.4 g, 58.05 mmol) and NaHCO3 (0.195 g, 2.32 mmol) and the reaction stirred at 150 0C until CO2 evolution stopped. The reaction mixture was then poured slowly into Et2O (200 mL). The ether layer was decanted and the residue was washed twice with ether (50 mL). The solid dissolved in hot EtOAc:MeOH:EtOH (4:1:1) mixture, filter and keep cool <n="41"/>overnight. A solid separated out, which was filtered and dried to afford 4.36 g (47percent yield) of a shiny brown solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydrogencarbonate In N,N-dimethyl-formamide for 1 h; Heating / reflux | 2,2'-Anhydro[1-(beta-D-arabinofuranosyl)-5-methyluridine] 5-Methyluridine (ribosylthymine, commercially available through Yamasa, Choshi, Japan) (72.0 g, 0.279 M), diphenylcarbonate (90.0 g, 0.420 M) and sodium bicarbonate (2.0 g, 0.024 M) were added to DMF (300 mL). The mixture was heated to reflux, with stirring, allowing the evolved carbon dioxide gas to be released in a controlled manner. After 1 hour, the slightly darkened solution was concentrated under reduced pressure. The resulting syrup was poured into diethylether (2.5 L), with stirring. The product formed a gum. The ether was decanted and the residue was dissolved in a minimum amount of methanol (ca. 400 mL). The solution was poured into fresh ether (2.5 L) to yield a stiff gum. The ether was decanted and the gum was dried in a vacuum oven (60° C. at 1 mm Hg for 24 h) to give a solid that was crushed to a light tan powder (57 g, 85percent crude yield). The NMR spectrum was consistent with the structure, contaminated with phenol as its sodium salt (ca. 5percent). The material was used as is for further reactions (or it can be purified further by column chromatography using a gradient of methanol in ethyl acetate (10-25percent) to give a white solid, mp 222-4° C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With bis(phenyl) carbonate; sodium carbonate In N,N-dimethyl-formamide at 110℃; | EXAMPLE 1 Synthesis of 2,2,-Anhydro-5-methyluracil 5-Methyl uridine (56.0 g, 217 mmol) and diphenyl carbonate (69.7 g, 325 mmol) were dissolved in DMF (250 mL) after which sodium bicarbonate (1.82 g, 22 mmol) was added to the solution. The resulting suspension was immersed in an oil bath and heated with stirring for 2.5-3 hrs at 1 10°C until cessation of CO2 evolution was observed. After cooling to room temperature the reaction mixture was concentrated to half volume and then slowly poured into rapidly stirring diethyl ether (800 mL) generating a white solid. After decanting the ether the white solid was washed with additional fresh ether (3 x 500 mL). The resulting solid was filtered, and washed with ether. A final precipitation was done by dissolving the isolated white solid in hot methanol (250 mL) and allowing the solution to cool to room temperature. Product was precipitated by addition of ether (250 mL), and then cooled at 0°C overnight. The white solid was isolated by filtration and dried on high vacuum to generate 2,2'-Anhydro-5- methyluracil (39.2 g, 75percent) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With acetic anhydride In pyridine; methanol; ethyl acetate; benzene | Example 3 Converting 2,2'-anhydrothymidine of the formula (X) to 3'5'-di-O-acetyl-2,2'-anhydrothymidine of the formula (XI) To a solution of 4 gm of anhydrothymidine in 15 ml of pyridine was added 5.1 gm of acetic anhydride. The mixture was shifted at room temperature for 3hrs when TLC (1:9 MeoH in EtOAc) showed no anhydrothymidine. The reaction was quenched with 10 ml of methanol and the solvents removed under vacuo. The brown semi solid is refluxed thrice in 50 ml benzene to yield 5.1 gm (94percent) of 3'5'-di-O-acetyl-2,2'-anhydrothymidine of the formula (XI). m.p. 168-172°C. |