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CAS No. : | 16597-50-5 | MDL No. : | MFCD00077041 |
Formula : | C19H21NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VBKUVUJWFDXTMS-PBHICJAKSA-N |
M.W : | 343.37 | Pubchem ID : | 7018808 |
Synonyms : |
|
Num. heavy atoms : | 25 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.26 |
Num. rotatable bonds : | 10 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 91.66 |
TPSA : | 84.86 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.52 cm/s |
Log Po/w (iLOGP) : | 2.94 |
Log Po/w (XLOGP3) : | 2.64 |
Log Po/w (WLOGP) : | 2.1 |
Log Po/w (MLOGP) : | 2.13 |
Log Po/w (SILICOS-IT) : | 2.55 |
Consensus Log Po/w : | 2.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.33 |
Solubility : | 0.162 mg/ml ; 0.000471 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.07 |
Solubility : | 0.029 mg/ml ; 0.0000846 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.03 |
Solubility : | 0.00322 mg/ml ; 0.00000938 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.71 |
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 |
---|---|---|
89.8% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 20h; | A mixture of 2-propylpentanoic acid (valproic acid, 4.32 g, 30 mmole), N- carbobenzyloxy-L-threonine benzyl ester (Z-Thr-OBzl, 10.30 g, 30 mmole), EDC (5.74 g, 30 mmole), and DMAP (366 mg, 3.0 mmole) in anhydrous dichloromethane (30 mL) was stirred under an argon atmosphere at room temperature for 20 hours. After 20 hours, the dichloromethane was washed with water (3x30 mL), dried over magnesium sulfate (5 g), filtered and concentrated under reduced pressure. The remaining colorless oil (13.44 g) was purified by column chromatography on silica gel (100 g, 0.035-0. 070 mm, 6 nm pore diameter), eluting with hexanes/ethyl acetate (4: 1). After concentration of the product containing fractions under reduced pressure and drying under high vacuum until the weight was constant, the experiment produced the protected L-threonine-valproate ester SPIC00301 (12.65 g, 89.8% yield) as a colorless oil. 'H NMR (300 MHz, CDCl3) : 8 = 7.40-7. 05 (11H, m), 5.45 (1H, m), 5.17-5. 02 (4H, m), 4.53 (1H, d, J= 9.6 Hz), 2.24 (1H, m), 1.58-1. 40 (2H, m), 1.40-1. 15 (9H, m), 0.86 (6H, m). 13C NMR (75 MHz, DMSO): 8 = 174. 24,169. 29,156. 48, 136.61, 135.34, 128.26, 128.20, 127.74, 127.67, 127.58, 69.04, 66.33, 65.78, 57.62, 44.50, 33.89, 33.80, 20.03, 19. 91, 16.40, 13.87. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.3% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 19h; | (+)-Ibuprofen (4.15 g, 20.11 mmole), N-carbobenzyloxy-L-threonine benzyl ester (6.90 g, 20.11 mmole), 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide, hydrochloride (EDC, 3.95 g, 20.6 mmole), and 4-(N, N-dimethylamino)-pyridine (DMAP, 0.25 g, 2.0 mmole) were dissolved in dichloromethane (50 mL) at room temperature, under an argon atmosphere. After stirring for 19 hours, the dichloromethane layer was washed with water (50 mL), 5% hydrochloric acid (2x25 mL), water (25 mL), saturated sodium bicarbonate (2x25 mL), and water (50 mL). After drying for one hour over sodium sulfate (5 g), filtration, and concentration under reduced pressure, the remaining oil was used without further purification. The procedure generated the protected L-threonine- ()-Ibuprofen ester (SPI001601) as a light yellow oil (10.2 g, 95.3% yield), which solidified on standing. 2 (S)-Benzyloxycarbonylamino-3- [2 (R, S)- (4-isobutyl-phenyl)-propionyloxy]-butyric acid benzyl ester: 'H NMR (300 MHz, CDC13) : a = 7.40-7. 15 (m, 10H), 7.14-7. 01 (m, 4H), 5.48-5. 25 (m, 2H), 5.11-5. 01 (m, 3H), 4.90 (d, 1/2H, J= 12 Hz), 4.68 (d, l/2H, J= 12 Hz), 4.48 (m, 1H), 3.60-3. 48 (m, 1H), 2.39 (m, 2H), 1.79 (m, 1H), 1.42-1. 35 (m, 3H), 1.27 (d, 1.5 H, J= 6. 6 Hz), 1.17 (d, 1.5 H, J= 6.6 Hz), 0. 85 (m, 6 H). 3C NMR (75 MHz, CDC13) : 8 = 173. 32,169. 70,169. 30,156. 55,140. 75,137. 38, 137.22, 136.14, 135.07, 134.99, 129.45, 129.41, 128.65, 128.39, 128.22, 127.21, 127.14, 70.97, 70.70, 67.81, 67.66, 67.53, 57.83, 45.19, 30.39, 22.61, 18.57, 18.30, 17.18, 16.87 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With pyridine; In dichloromethane; at 0 - 20℃; for 24h; | A mixture of N-carbobenzyloxy-L-threonine benzyl ester (Z-Thr-OBzl, 21.77 g, 63.40 mmole) and pyridine (25 mL) in anhydrous dichloromethane (500 mL) was cooled in an ice bath while under a nitrogen atmosphere. Acetylsalicyloyl chloride (17.63 g, 88.76 mmole) was added and the mixture was allowed to warm to room temperature and stir overnight. After 24 hours, the mixture was poured into ice-cold 2N hydrochloric acid (400 mL). After mixing, the layers were separated and the dichloromethane fraction was washed with water (500 mL), saturated sodium bicarbonate solution (500 mL), water (500 mL), brine (500 mL) and dried over sodium sulfate (25 g). After filtration, concentration under reduced pressure, and drying under high vacuum, the remaining yellow oil (35.43 g) was purified by flash chromatography on silica gel (300 g, 0.035- 0.070 mm, 6 nm pore diameter), eluting with hexanes/ethyl acetate (3: 1). After concentration of the product containing fractions under reduced pressure and drying under high vacuum until the weight was constant, the experiment produced the protected acetylsalicylic-L-threonine ester SPIB0010201 (28.1 g, 88% yield) as a colorless oil. IH NMR (300 MHz, CDC13) : 5 = 7.74 (1H, d, J= 7. 5 Hz), 7.51 (1H, dt, J= 7. 5,1. 5 Hz), 7. 34-7. 17 (lah, m), 7.06 (1H, d, J= 7. 2 Hz), 5.62 (2H, m), 5.13 (4H, m), 4.65 (1H, dd, J= 9.6, 2.4 Hz), 2.29 (3H, s), 1. 38 (3H, d, J= 6.6 Hz). 3C NMR (75 MHz, CDC13) : 8 = 169.35, 169.22, 162.73, 156.26, 150.41, 135.79, 134.67, 133.77, 131.24, 128.35, 128.24, 128.08, 127.95, 125.78, 123.51, 122.61, 71.22, 67.72, 67.26, 57.64, 20.98, 16. 88. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 4h; | S- (+)-Ibuprofen (2.0 g, 9.69 mmole), N-carbobenzyloxy-L-threonine benzyl ester (3.25 g, 9.91 mmole), 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide, hydrochloride (EDC, 1.90 g, 9.91 mmole), and 4- (N, N-dimethylamino) -pyridine (DMAP, 0.12 g, 1.0 mmole) were dissolved in dichloromethane (25 mL) at room temperature, under an argon atmosphere. After stirring for 4 hours, the dichloromethane layer was washed with water (25 mL), 5% hydrochloric acid (25 mL), saturated sodium bicarbonate (2x25 mL), and water (25 mL). After drying for one hour over sodium sulfate (5 g), filtration, and concentration under reduced pressure, the remaining oil was used without further purification. The procedure generated the protected S- (+)-Ibuprofen-L-threonine ester (SPI001601S) as a light yellow oil (5.01 g, 98 % yield), which solidified on standing. 2 (S)-Benzyloxycarbonylamino-3- [2 (R, S)- (4-isobutyl-phenyl)-propionyloxy]-butyric acid benzyl ester: IH NMR (300 MHz, CDC13) : 6 = 7.35-7. 23 (m, lOH), 7.10 (d, 2H, J= 7. 8 Hz), 7.05 (d, 2H, J= 7. 8 Hz), 5.48-5. 25 (m, 2H), 5.17-5. 01 (m, 4H), 4.50 (dd, 1H, J= 9. 6,1. 8 Hz), 3.50 (q, 1H, J= 7. 2 Hz), 2.40 (d, 2H, J= 7. 2 Hz), 1.80 (m, 1H), 1.37 (d, 3H, J= 7.2 Hz), 1.17 (d, 3 H, J= 6.3 Hz), 0.86 (d, 6 H, J= 6.6 Hz). 3C NMR (75 MHz, CDC13) : 8 = 173. 29,169. 69,156. 51,140. 68,137. 21,136. 08, 135.06, 129.40, 128.70, 128.66, 128.57, 128.38, 128.24, 127.14, 70.70, 67.80, 67.53, 57.87, 45.19, 45.11, 30.39, 22. 61, 18.57, 16. 87 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: N-benzyloxycarbonyl-L-threonine benzyl ester; N-((2S,3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(phenylthio)tetrahydro-2H-pyran-3-yl)-2,2,2-trichloroacetamide With copper(I) trifluoromethanesolfonate toluene complex In 1,2-dichloro-ethane at 0℃; for 0.25h; Molecular sieve; Stage #2: In 1,2-dichloro-ethane at 23℃; for 2h; Molecular sieve; | 4.1 General glycosylation procedure General procedure: A 10mL vial containing the peptide acceptor (0.10mmol), copper(I) triflate (commercial toluene complex, 10.5mg, 0.02mmol), activated 4 molecular sieves (150mg), the glycosyl donor (0.15mmol) and 1,2-dichloroethane (1mL) was stirred at 0°C (external ice bath) for 15min. N-iodosuccinimide (45mg, 0.20mmol) was added, and the reaction mixture was allowed to stir at 0°C or room temperature for 2h as needed for disappearance of donor. The reaction mixture was filtered through a 0.45μM PTFE syringe filter, and the cake was rinsed with dichloromethane (2×5mL). The organic solution was washed with 10mL of saturated aq sodium bisulfite, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by using a pre-packed silica gel column or preparative silica thin layer chromatography plate to afford the glycosylation product. |
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