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CAS No. : | 87-91-2 | MDL No. : | MFCD00009143 |
Formula : | C8H14O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YSAVZVORKRDODB-PHDIDXHHSA-N |
M.W : | 206.19 | Pubchem ID : | 6993580 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 45.46 |
TPSA : | 93.06 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) : | -7.76 cm/s |
Log Po/w (iLOGP) : | 1.88 |
Log Po/w (XLOGP3) : | -0.29 |
Log Po/w (WLOGP) : | -1.17 |
Log Po/w (MLOGP) : | -0.71 |
Log Po/w (SILICOS-IT) : | -0.22 |
Consensus Log Po/w : | -0.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.47 |
Solubility : | 69.3 mg/ml ; 0.336 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.2 |
Solubility : | 12.9 mg/ml ; 0.0624 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.2 |
Solubility : | 330.0 mg/ml ; 1.6 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.14 |
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 |
---|---|---|
60% | Stage #1: With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In ethyl acetate at 20℃; for 3 h; Stage #2: With ammonium acetate In water; acetic acid; ethyl acetate at 10 - 50℃; for 3.5 h; Cooling with ice |
(Reference Example 3) Diethyl 1H-imidazole-4,5-dicarboxylate Reference Example 3 was carried out under non-light-shielding conditions. To a solution of L-tartaric acid diethyl ester (2.0 g) in ethyl acetate (34.2 ml), 1,3-dibromo-5,5-dimethylhydantoin (3.3 g) was added, and the reaction solution was stirred at room temperature for 3 hours. To the reaction solution, acetic acid (17 ml) was added, and subsequently 36percent aqueous formaldehyde solution (3.45 ml) was added under ice cooling at an internal temperature of 10°C or below, followed by addition of ammonium acetate (17.2 g) at an internal temperature of 10°C or below. The reaction solution was stirred at room temperature for 30 minutes, followed by stirring at 50°C for 3 hours. To the reaction solution, 5N sodium hydroxide was added, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, and dried over magnesium sulfate. Quantitative analysis of the resulting ethyl acetate solution by HPLC showed that the title compound (1.24 g, yield: 60percent) was obtained. Condition for HPLC analysis is identical with that for Example 5. From the results of Reference Example 3 and Example 5, it was shown that the production method of the present invention [the method for producing compound (5) from compound (1)] was superior to the reaction indicated in the known Method X in terms of yield even under non-light-shielding conditions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.5 % ee | With (S)-aminopropyl alcohol(at)silica 1 In hexane; isopropyl alcohol at 20℃; for 1 h; Resolution of racemate; Inert atmosphere | Example-32; To a medium pressure chromatographic column, slurry of (S)-aminopropyl alcohol(at)silica 1 (0.512 mol percent) in hexane and isopropanol (8:2) was packed in a 260.x.16 mm glass column using medium-pressure (0.5 kp/cm2) of nitrogen at room temperature. The solution of racemic diethyl-tartrate (0.50 mol percent) in isopropanol/hexane (1:1) was loaded on packed column that was equilibrated for 1 h. The elution of fractions was done at the pressure mentioned above. Each fraction was subjected to HPLC analysis using an appropriate Chiralpak AD column, eluent hexane/isopropanol (8:2) at 220nm. The enantiomeric excess of diethyl-tartrate found 11.5percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.2% | at 0 - 50℃; for 3.5 h; | (1)Into 500mL three-necked glass flask L - (+) - tartaric acid 30g,Then take the amount of anhydrous ethanol 150mL added to three-necked flask,Turn on stirringControl the internal temperature at 0 ~ 30 ,95.4 g of thionyl chloride was added dropwise,Time is 1.5h,Dropping the process of exothermic,After the addition was completed, the temperature was raised to 50 ° C,Reaction 2h,Then vacuum distillation,Remove ethanol,Get L - (+) - diethyl tartrate crude;(2)To the L - (+) - diethyl tartrate crude was added potassium bicarbonate 3.3g,Warmed to 20 ° C,Stirring reaction 3h,Filter to remove the solid,39.6 g of L - (+) - tartaric acid diethyl ester was obtained as a colorless or light yellow oily liquid,The molar yield was 96.2percentAfter testing,Product purity is 99.4percent. |
94% | at 25℃; for 12 h; Cooling with ice | (1) under the ice water bath, to tartaric acid L - (substituted (I - 1 - 1), 100 g, 0.67 µM) anhydrous ethanol (600 ml) is dropped in the adds the chlorination sulfoxide (107 ml), at room temperature (about 25 °C) reaction 12 h, at low temperature the solvent is removed under reduced pressure, dissolved in EtOAc, saturated sodium bicarbonate washing to neutral, dried, concentrated under reduced pressure to remove the solvent, and concentration to obtain a colorless oil of, substituted (I - 1 - 2) compound of formula (138 g, yield 94percent). |
88% | for 10 h; Reflux | A mixture of (2R,3R)-(+)-tartaric acid 1 (22.0 g, 150 mmol) and a catalytic amount of H2SO4 in EtOH (100 mL) was stirred at reflux for 10 h. After completion of the reaction, the mixture was concentrated in vacuo. A silica gel mesh was prepared from the residue and submitted to flash chromatography (silica gel: EtOAc/hexane as eluent) to provide 2 (26.4 g, 88percent). 1H-NMR (CDCl3, δ=7.26 ppm, 400 MHz,): 1.27 (t, J = 7.2 Hz, 6H), 3.36 (d, J = 6.6 Hz, 2H), 4.26 (q, J = 7.2 Hz, 4H), 4.5 (d, J = 6Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.5 % ee | With (S)-aminopropyl alcohol(at)silica 1 In hexane; isopropyl alcohol at 20℃; for 1 h; Resolution of racemate; Inert atmosphere | Example-32; To a medium pressure chromatographic column, slurry of (S)-aminopropyl alcohol(at)silica 1 (0.512 mol percent) in hexane and isopropanol (8:2) was packed in a 260.x.16 mm glass column using medium-pressure (0.5 kp/cm2) of nitrogen at room temperature. The solution of racemic diethyl-tartrate (0.50 mol percent) in isopropanol/hexane (1:1) was loaded on packed column that was equilibrated for 1 h. The elution of fractions was done at the pressure mentioned above. Each fraction was subjected to HPLC analysis using an appropriate Chiralpak AD column, eluent hexane/isopropanol (8:2) at 220nm. The enantiomeric excess of diethyl-tartrate found 11.5percent. |
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