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CAS No. : | 635728-49-3 | MDL No. : | |
Formula : | C29H43N3O8S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QWSHKNICRJHQCY-VBTXLZOXSA-N |
M.W : | 593.73 | Pubchem ID : | 23725083 |
Synonyms : |
TMC114 Ethanolate;Darunavir (ethanolate);UIC 94017;TMC-114
|
Num. heavy atoms : | 41 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.55 |
Num. rotatable bonds : | 13 |
Num. H-bond acceptors : | 9.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 155.09 |
TPSA : | 169.03 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.9 cm/s |
Log Po/w (iLOGP) : | 4.67 |
Log Po/w (XLOGP3) : | 2.85 |
Log Po/w (WLOGP) : | 3.46 |
Log Po/w (MLOGP) : | 0.81 |
Log Po/w (SILICOS-IT) : | 1.46 |
Consensus Log Po/w : | 2.65 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 2.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -4.68 |
Solubility : | 0.0125 mg/ml ; 0.0000211 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.06 |
Solubility : | 0.000519 mg/ml ; 0.000000874 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -5.33 |
Solubility : | 0.00276 mg/ml ; 0.00000466 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 6.04 |
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 |
---|---|---|
82.5% | Stage #1: at -4 - 30℃; for 10 h; Stage #2: at 45 - 50℃; for 1 h; |
A solution of (3R,3aS,6aR)-hexahydrofuro[2,3-t]furan-3-yl 4-nitrophenyl carbonate (5b, 75.4 g) in N-methyl-2-pyrrolidinone (300 mL) was added to a pre-cooled (-2±2° C.) solution of the compound of formula 4 (100 g) in N-methyl-2-pyrrolidinone (200 mL) at -4 to 0° C. over a period of 2 h. The temperature of the reaction mass was slowly raised to 25-30° C. and maintained for 8 h. After completion of the reaction (TLC monitoring), ethyl acetate (1000 mL) and purified water (500 mL) were added to the reaction mass. The layers were separated; organic layer was washed with sodium carbonate solution (2*500 mL) followed by sodium chloride solution. The organic layer was concentrated; ethanol (300 mL) was added, heated to 45-50° C., maintained for 1 h, filtered and washed with ethanol. The wet compound was taken into a mixture of ethyl acetate-ethanol (7:93, 600 mL), heated to reflux, charcoal was added and filtered. The resultant filtrate was cooled to 0-5° C., filtered the separated solid and washed with ethanol. The wet compound was dried at 45° C. to obtain the in 124.3 g (yield-82.5percent). The obtained Darunavir ethanolate had purity of 99.79percent on area by HPLC and contained 0.08percent on area by HPLC of the difuranyl impurity. |