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[ CAS No. 16597-50-5 ] {[proInfo.proName]}

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Chemical Structure| 16597-50-5
Chemical Structure| 16597-50-5
Structure of 16597-50-5 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 16597-50-5 ]

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Product Details of [ 16597-50-5 ]

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 :

Calculated chemistry of [ 16597-50-5 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.71

Safety of [ 16597-50-5 ]

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:

Application In Synthesis of [ 16597-50-5 ]

* 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.

  • Downstream synthetic route of [ 16597-50-5 ]

[ 16597-50-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 99-66-1 ]
  • [ 84500-41-4 ]
  • [ 852056-03-2 ]
YieldReaction ConditionsOperation 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.
  • 2
  • [ 15687-27-1 ]
  • [ 84500-41-4 ]
  • [ 852055-78-8 ]
YieldReaction ConditionsOperation 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
  • 3
  • [ 84500-41-4 ]
  • [ 5538-51-2 ]
  • [ 852055-87-9 ]
YieldReaction ConditionsOperation 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.
  • 4
  • [ 84500-41-4 ]
  • [ 51146-56-6 ]
  • [ 852055-81-3 ]
YieldReaction ConditionsOperation 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
  • 5
  • [ 16597-50-5 ]
  • [ 2225957-74-2 ]
  • [ 2225957-78-6 ]
YieldReaction ConditionsOperation 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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