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[ CAS No. 57044-25-4 ] {[proInfo.proName]}

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Type HazMat fee for 500 gram (Estimated)
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Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 57044-25-4
Chemical Structure| 57044-25-4
Structure of 57044-25-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 57044-25-4 ]

CAS No. :57044-25-4 MDL No. :MFCD00074873
Formula : C3H6O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CTKINSOISVBQLD-GSVOUGTGSA-N
M.W : 74.08 Pubchem ID :5460455
Synonyms :

Calculated chemistry of [ 57044-25-4 ]

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 16.67
TPSA : 32.76 Ų

Pharmacokinetics

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) : -7.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.0
Log Po/w (XLOGP3) : -0.95
Log Po/w (WLOGP) : -0.62
Log Po/w (MLOGP) : -1.03
Log Po/w (SILICOS-IT) : 0.76
Consensus Log Po/w : -0.17

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.37
Solubility : 172.0 mg/ml ; 2.32 mol/l
Class : Highly soluble
Log S (Ali) : 0.75
Solubility : 413.0 mg/ml ; 5.58 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.36
Solubility : 171.0 mg/ml ; 2.31 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 57044-25-4 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P260-P270-P202-P210-P201-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P308+P311-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P311-P403+P233-P403+P235-P405 UN#:2810
Hazard Statements:H331-H302+H312-H315-H319-H361-H370-H373-H341-H350-H335-H227 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 57044-25-4 ]

* 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 [ 57044-25-4 ]
  • Downstream synthetic route of [ 57044-25-4 ]

[ 57044-25-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 57044-25-4 ]
  • [ 61278-21-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 22, p. 3707 - 3716
[2] Synlett, 2000, # 5, p. 635 - 636
[3] Tetrahedron Letters, 2016, vol. 57, # 13, p. 1486 - 1488
[4] Tetrahedron Letters, 2015, vol. 56, # 48, p. 6659 - 6663
  • 2
  • [ 4826-71-5 ]
  • [ 57044-25-4 ]
  • [ 28319-77-9 ]
YieldReaction ConditionsOperation in experiment
289 g
Stage #1: With sodium carbonate In water at 20℃; for 1 h;
Stage #2: Reflux
Add in the reactorPhosphorylcholine calcium salt (usually tetrahydrate) 330g and 300ml water,Stir until dissolvedA sodium carbonate solution with a concentration of 50percent made of anhydrous sodium carbonate (106 g) and water was dropped and dropped at a rate of 10 ml/min. After the dropwise addition, the mixture was stirred at room temperature for 1 hour. The salt solution was passed according to the solubility of sodium chloride. Precipitation of sodium chloride in the reaction systemfilter. The filtrate was passed through a sulfonic acid ion column and eluted with water several times to HPLC without product.The solvent was distilled under reduced pressure and concentrated to a volume of 300 ml.66 g of (R)-chiral glycidol was added, and the reaction was stirred at reflux for 2-6 hours. HPLC showed no raw material, and the water was evaporated under reduced pressure and recrystallized from methanol to obtain 289 g of product. (HPLC > 99.7percent)
Reference: [1] Patent: CN104628766, 2017, B, . Location in patent: Paragraph 0044; 0045; 0046; 0047; 0048; 0049; 0050-0059
  • 3
  • [ 98-59-9 ]
  • [ 57044-25-4 ]
  • [ 113826-06-5 ]
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
  • 4
  • [ 121-51-7 ]
  • [ 57044-25-4 ]
  • [ 115314-14-2 ]
YieldReaction ConditionsOperation in experiment
97% at -20℃; for 96 h; [0251] m-Nitrobenzensulfonylchloride (12.6 g; 57 mmol) was added to a cold (-20° C.) solution of (R)-(+)-glycidol (5.5 g; 74 mmol) and TEA (10.3 mL; 74 mmol). The reaction mixture was stirred at -20° C. for 96 h. The solution was filtered and the filtrate washed with tartaric acid (10percent w/w), brine, H2O and concentrated giving the title compound in a 97percent yield. [0252] 1H NMR (CDCl3): δ 2.62 (dd, 1H), 2.84 (dd, 1H), 3.22 (m, 1H), 4.07 (dd, 1H), 4.49 (dd, 1H), 7.80 (t, 1H), 8.25 (m, 1H), 8.52 (m, 1H), 8.78 (m, 1H)
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5305 - 5308[2] Angew. Chem., 2013, vol. 125, # 20, p. 5413 - 5416,4
[3] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4053 - 4069
[4] Patent: US2004/229900, 2004, A1, . Location in patent: Page 14
[5] Organic and Biomolecular Chemistry, 2006, vol. 4, # 16, p. 3067 - 3076
[6] Patent: US5096904, 1992, A,
  • 5
  • [ 2461-40-7 ]
  • [ 60456-26-0 ]
  • [ 57044-25-4 ]
YieldReaction ConditionsOperation in experiment
> 99 % ee With thermomyces lanuginosa In 1,4-dioxane; aq. phosphate buffer at 30℃; for 2 h; Resolution of racemate; Enzymatic reaction General procedure: In a 50 mL erlenmeyer flask containing 6 mL of phosphate buffer (1 M, pH 7), it was added the ester (0.36 mmol), lipase (5 mg), and dioxane (0.6 mL). The mixture was shaken (150 rpm) at 30 °C or 50 °C for a specified period of time (Table 2), while the pH was maintained at 7 by the periodic addition of aqueous 1 M solution of NaOH. It was considered 50percent hydrolysis of the substrate when half the equimolar amount of NaOH was consumed and, an aliquot of the reaction mixture was taken and analyzed by chiral HPLC or GC.
Reference: [1] Tetrahedron Asymmetry, 2005, vol. 16, # 4, p. 869 - 874
[2] Tetrahedron Letters, 2015, vol. 56, # 13, p. 1696 - 1698
  • 6
  • [ 2461-40-7 ]
  • [ 60456-26-0 ]
  • [ 57044-25-4 ]
  • [ 60456-23-7 ]
Reference: [1] Tetrahedron Asymmetry, 2004, vol. 15, # 7, p. 1157 - 1161
  • 7
  • [ 76-83-5 ]
  • [ 57044-25-4 ]
  • [ 129940-50-7 ]
YieldReaction ConditionsOperation in experiment
73% With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere; Cooling Trityl protected glycidol derivative 401 was prepared as described previously (Schweizer, et al., Synthesis 2007, 3807-3814; which is incorporated herein by reference.) A solution of (/?)-glycidol (5.0 g, 61 mmol) in CH2Cl2 (30 mL) was added by syringe to a stirred solution of trityl chloride (18.6 g, 66.8 mmol) and triethylamine (16.9 mL, 122 mmol) in CH2Cl2 (67 mL) in an ice bath under argon. DMAP (742 mg, 6.08 mmol) was added to the reaction mixture following addition of the glycidol. The reaction was allowed to warm to room temperature. After 14 hours, the reaction mixture was diluted with 300 mL saturated aqueous NH4CI. The mixture was further diluted to ~ 1 L with water to dissolve precipitated salts. The product was extracted from the quenching solution with Et2O (3 x); combined ethereal layers were washed with brine, dried over MgSO4, filtered through paper, and concentrated by rotary evaporation to a white solid. The crude product was purified by recrystallization from boiling MeOH (200 mL) affording the desired product 401 (14.1 g, 73percent) as white crystals. NMR analysis of this material was consistent with that reported in the literature. (Schweizer, et al., Synthesis 2007, 3807-3814.)
Reference: [1] Synthesis, 2007, # 24, p. 3807 - 3814
[2] Tetrahedron Letters, 2000, vol. 41, # 33, p. 6323 - 6326
[3] Journal of Organic Chemistry, 2003, vol. 68, # 8, p. 3026 - 3042
[4] Journal of Organic Chemistry, 2013, vol. 78, # 11, p. 5172 - 5183
[5] Patent: WO2010/53572, 2010, A2, . Location in patent: Page/Page column 163
[6] ACS Chemical Neuroscience, 2018,
[7] Tetrahedron Letters, 1994, vol. 35, # 20, p. 3243 - 3246
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 16, p. 2229 - 2236
[9] Journal of Organic Chemistry, 1998, vol. 63, # 6, p. 1961 - 1973
[10] Tetrahedron Letters, 1999, vol. 40, # 12, p. 2371 - 2374
[11] Patent: WO2006/14429, 2006, A2, . Location in patent: Page/Page column 11; figure 3
  • 8
  • [ 136918-14-4 ]
  • [ 57044-25-4 ]
  • [ 181140-34-1 ]
YieldReaction ConditionsOperation in experiment
75% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; To a solution of phthalimide (6.6 g, 45.0 mmol) in THF (220 mL) was added PPh3 (17.7 g, 67.5 mmol), DEAD (11.7 ml, 67.5 mmol), and (R)-(+)-glycidol (4.0 g, 54.0 mmol). This mixture was stirred at room temperature overnight. THF was removed and the residue was purified by flash column chromatography on silica gel (Biotage, 5percent-20percent EtOAc/hexane) to provide the title compound (5.8 g, 75percent).
Reference: [1] Tetrahedron Asymmetry, 1996, vol. 7, # 6, p. 1641 - 1648
[2] Patent: WO2006/29210, 2006, A2, . Location in patent: Page/Page column 112-113
[3] Heterocycles, 2006, vol. 67, # 2, p. 561 - 566
[4] Tetrahedron, 2004, vol. 60, # 35, p. 7679 - 7692
[5] Patent: US2006/14701, 2006, A1, . Location in patent: Page/Page column 23
  • 9
  • [ 136918-14-4 ]
  • [ 57044-25-4 ]
  • [ 161596-47-0 ]
YieldReaction ConditionsOperation in experiment
53% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 4 h; To a solution of triphenylphosphine (17.7 g, 67.5 mmol), (R)-(+)-glycidol (4.0 g,54.0 mmol), and phthalamide in THF (220 mL) was added DEAD (11.7 g, 67.5 mmol). The reaction mixture was stirred under nitrogen at RT for 4 hr. After evaporating solvent, EPO <DP n="100"/>the crude product was purified by flash column chromatography to provide 5.8 g (53percent) of the desired product; LCMS: [MH]+ = 204.
Reference: [1] Patent: WO2007/30761, 2007, A2, . Location in patent: Page/Page column 37; 98-99
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