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[ CAS No. 113826-06-5 ] {[proInfo.proName]}

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Chemical Structure| 113826-06-5
Chemical Structure| 113826-06-5
Structure of 113826-06-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 113826-06-5 ]

CAS No. :113826-06-5 MDL No. :MFCD00010834
Formula : C10H12O4S Boiling Point : -
Linear Structure Formula :- InChI Key :NOQXXYIGRPAZJC-SECBINFHSA-N
M.W : 228.26 Pubchem ID :154187
Synonyms :

Calculated chemistry of [ 113826-06-5 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.17
TPSA : 64.28 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 1.14
Log Po/w (WLOGP) : 2.18
Log Po/w (MLOGP) : 1.16
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.01
Solubility : 2.25 mg/ml ; 0.00988 mol/l
Class : Soluble
Log S (Ali) : -2.08
Solubility : 1.88 mg/ml ; 0.00824 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.92
Solubility : 0.273 mg/ml ; 0.00119 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.26

Safety of [ 113826-06-5 ]

Signal Word:Danger Class:9
Precautionary Statements:P201-P273-P280-P302+P352-P305+P351+P338+P310-P308+P313 UN#:3077
Hazard Statements:H317-H318-H341-H350-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 113826-06-5 ]

* 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.

  • Upstream synthesis route of [ 113826-06-5 ]
  • Downstream synthetic route of [ 113826-06-5 ]

[ 113826-06-5 ] Synthesis Path-Upstream   1~6

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Reference: [1] Patent: CN105418546, 2016, A, . Location in patent: Paragraph 0100; 0101; 0102
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  • [ 107-18-6 ]
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Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 19, p. 3710 - 3712
[2] Journal of the American Chemical Society, 1987, vol. 109, # 19, p. 5765 - 5780
  • 3
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YieldReaction ConditionsOperation in experiment
85% With triethylamine In dichloromethane at 0℃; for 3 h; Paratoluenesulfonyl chloride (PTSC, 25.0 g) and (R)-oxiran-2-ylmethanol (6.0 mL) were dissolved in anhydrous dichloromethane (DCM, 250 mL), then, triethylamine (TEA, 36.0 mL) was dropwise added in the mixture at 0 °C.
After reacting for 3 h at 0 °C, the reaction liquid was concentrated.
At last, the residue was purified by flash column chromatography with ethyl acetate/petroleum ether to obtain the title compound 2 (17.6 g). White solid; yield:85.0percent; mp: 44–46 C; [a]D25 = +18.3 (c 1.7, acetonitrile). IR (KBr)1598, 1363, 1177, 969, 666, 556. 1H NMR (400 MHz, DMSO-d6) d7.83 (d, J = 8.1 Hz, 2H), 7.52–7.46 (m, 2H), 4.43 (d, J = 11.6 Hz, 1H), 3.85 (dddd, J = 7.0, 5.7, 3.7, 1.9 Hz, 1H), 3.26–3.17 (m, 1H), 2.78(t, J = 4.6 Hz, 1H), 2.66–2.58 (m, 1H), 2.42 (s, 3H). ESI-MS m/z: 251.2[M+Na]+.
85% With triethylamine In dichloromethane at 0℃; for 3 h; Tosyl chloride (25.0 g) was dissolved in redissolved dichloromethane (250 mL) and (R)-glycidol (6.0 mL) was added to the solution.Triethylamine (36.0 mL) was added dropwise to the reaction solution at 0° C. The reaction was carried out for 3 hours, evaporated to dryness and passed through the column. This gave 17.6 g of a white solid with a yield of 85.0percent.
78% With hydrogenchloride; sodium hydroxide; N,N-dimethylamino-pyridine In water; toluene Example 4
Peparation of Optically Active Glycidyl Tosylate
To a solution of 6.7 g of (R)-glycidol (0.09 mol)(optical purity: 99.4percent ee) and 50 ml of water, 0.17 g of N,N-dimethylaminopyridine (0.0014 mol) and 17.2 g of p-toluenesulfonyl chloride (0.09 mol) in 50 ml of toluene, and then 18.1 g of 24percent sodium hydroxide (0.11 mol) were added under stirring at 0-5° C.
And the solution was stirred for one hour.
After separation with a separating funnel, the organic layer was washed with 50 ml of 1percent hydrochloric acid and 50 ml of water.
The excess solvent was removed under vacuo.
The chemical purity by HPLC and optical purity at that time were 99.5percent, 99.5percent ee respectively.
The residue was recrystallized from isopropyl alcohol/hexane=1/1 (V/V) to give 16.1 g of (S)-glycidyl tosylate (yield 78percent).
Chemical purity: 99.9percent, Optical purity: 99.6percent ee
99.5 % ee With triethylamine In dichloromethane at 0 - 20℃; for 1 h; To 1.2 L of a methylene chloride solution of (R)-3-chloro-l,2-propanediol (200g, 99.5percent ee) was added 499 g of potassium phosphate tribasic, and then the obtained solution was refluxed, under stirring, for 3 hours. The resulting solution was cooled to 0°C, and 201 g of triethylamine, 4 g of 4-(dimethylamino)pyridine, and tosyl chloride (69 g x 5) was added to the solution. After additional stirring for 1 hour at a room temperature, the reaction mixture was successively washed with 2.2 L of 5percent aqueous potassium carbonate solution, 2 L of IN aqueous hydrogen chloride solution, and 1 L of water. The organic layer was dried with 50 g of anhydrous sodium sulfate and filtrated. Evaporation of the methylene chloride under reduced pressure gave a crude product (chemical purity: 99.3percent, optical purity 99.5percent ee). After addition of hexane to the resulting residue, the obtained solid product was filtrated to give 337 g of the targeted product:-Yield: 81.5percent- Chemical purity: 99.8percent- Optical purity (GC) 99.5percent ee- Melting point: 47~49°C

Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8668 - 8676
[2] Chemical Communications, 2014, vol. 50, # 51, p. 6718 - 6721
[3] Organic Letters, 2012, vol. 14, # 11, p. 2834 - 2837
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 15, p. 3859 - 3862[5] Angew.Chem.Int.Ed., 2014, vol. 53, p. 3859 - 3862,4
[6] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 20, p. 6632 - 6640
[7] Patent: CN105130951, 2018, B, . Location in patent: Paragraph 0121; 0122
[8] Patent: US5965753, 1999, A,
[9] Patent: WO2006/19202, 2006, A1, . Location in patent: Page/Page column 7-8
[10] European Journal of Medicinal Chemistry, 2013, vol. 62, p. 329 - 340
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YieldReaction ConditionsOperation in experiment
70% With hydrogenchloride; N,N-dimethylamino-pyridine; potassium carbonate; triethylamine In water Comparative Example 3
To a suspension of 37.5 g of potassium carbonate (0.27 mol) and 250 ml of 1,2-dichloroethane, was added dropwise at 24-28° C. 20 g of (S)-3-chloro-1,2-propanediol (0.18 mol) (optical purity: 98.9percent ee).
After finishing the addition, the solution was stirred for 26 hours and cooled.
To the reaction solution were added dropwise under stirring at 5-10° C. 20.1 g of triethylamine (0.2 mol) and 0.4 g of N,N-dimethylaminopyridine (0.0033 mol) and 34.5 g of p-toluenesulfonyl chloride (0.18 ml) in order.
After finishing the addition the mixture was stirred for 3 hours and the resulting salt was dissolved by adding 150 ml of 3percent hydrochloric acid.
The organic layer was washed with 150 ml of 1percent hydrochloric acid and 150 ml of water.
The excess solvent was removed under vacuo.
The chemical purity and optical purity at that time were 93.7percent, 96.6percent ee respectively.
The residue was recrystallized from isopropyl alcohol/hexane=1/1 (V/V) to give 28.9 g of (S)-glycidyl tosylate (yield 70percent).
Chemical purity: 98.3percent, optical purity: 97.5percent ee
Reference: [1] Patent: US5965753, 1999, A,
  • 5
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Reference: [1] Patent: CN105418546, 2016, A, . Location in patent: Paragraph 0100; 0101; 0102
  • 6
  • [ 107-18-6 ]
  • [ 98-59-9 ]
  • [ 70987-78-9 ]
  • [ 113826-06-5 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 19, p. 3710 - 3712
[2] Journal of the American Chemical Society, 1987, vol. 109, # 19, p. 5765 - 5780
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