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[ CAS No. 4437-01-8 ] {[proInfo.proName]}

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Chemical Structure| 4437-01-8
Chemical Structure| 4437-01-8
Structure of 4437-01-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4437-01-8 ]

CAS No. :4437-01-8 MDL No. :MFCD06201006
Formula : C15H32O8 Boiling Point : -
Linear Structure Formula :- InChI Key :AGWKUHGLWHMYTG-UHFFFAOYSA-N
M.W :340.41 Pubchem ID :526555
Synonyms :
m-PEG7-alcohol

Calculated chemistry of [ 4437-01-8 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 20
Num. H-bond acceptors : 8.0
Num. H-bond donors : 1.0
Molar Refractivity : 82.98
TPSA : 84.84 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) : -9.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.38
Log Po/w (XLOGP3) : -1.49
Log Po/w (WLOGP) : -0.28
Log Po/w (MLOGP) : -1.68
Log Po/w (SILICOS-IT) : 2.37
Consensus Log Po/w : 0.66

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.31
Solubility : 692.0 mg/ml ; 2.03 mol/l
Class : Highly soluble
Log S (Ali) : 0.21
Solubility : 556.0 mg/ml ; 1.63 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -3.51
Solubility : 0.105 mg/ml ; 0.000309 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.34

Safety of [ 4437-01-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H319-H302-H335-H315 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4437-01-8 ]

* 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 [ 4437-01-8 ]
  • Downstream synthetic route of [ 4437-01-8 ]

[ 4437-01-8 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 112-60-7 ]
  • [ 74654-05-0 ]
  • [ 4437-01-8 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 1 h;
Stage #2: at 20℃; for 3.5 h;
To a stirred solution of non-polydispersed compound 11 (35.7 mmol) in dry DMF (25.7 ML), under N2 was added in portion a 60percent dispersion of NaH in mineral oil, and the mixture was stirred at room temperature for 1 hour.To this salt 12 was added a solution of non-polydispersed mesylate 9 (23.36) in dry DMF (4 ml) in a single portion, and the mixture was stirred at room temperature for 3.5 hours.Progress of the reaction was monitored by TLC (12percent CH3OH-CHCl3).The reaction mixture was diluted with an equal amount of 1N HCl, and extracted with ethyl acetate (2*20 ml) and discarded.Extraction of aqueous solution and work-up gave non-polydispersed polymer 10 (82-84percent yield).
41%
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran for 1.5 h;
To a solution of non-polydispersed tetraethylene glycol (51.5 g, 0.27 mol) in THF (1L) was added potassium t-butoxide (14.8 g, 0.13 mol, small portions over 30 min). The reaction mixture was then stirred for 1 h and then 24 (29.15 g, 0.12 mol) dissolved in THF (90 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed CH2Cl2, 200 mL) and evaporated to dryness. The oil was then dissolved in HCl (250 mL, 1 N) and washed with ethyl acetate (250 mL) to remove excess 24. Additional washings of ethyl acetate (125 mL) may be required to remove remaining 24. The aqueous phase was washed repetitively with CH2Cl2 (125 mL volumes) until most of the 25 has been removed from the aqueous phase. The first extraction will contain 24, 25, and dicoupled side product and should be back extracted with HCl (125 mL, 1N). The organic layers were combined and evaporated to dryness. The resultant oil was then dissolved in CH2Cl2 (100 mL) and washed repetitively with H20 (50 mL volumes) until 25 was removed. The aqueous fractions were combined, total volume 500 mL, and NaCl was added until the solution became cloudy and then was washed with CH2Cl2 (2.x.500 mL). The organic layers were combined, dried MgSO4, and evaporated to dryness to afford a the non-polydispersed title compound as an oil (16.9 g, 41percent yield). It may be desirable to repeat one or more steps of the purification procedure to ensure high purity.
41%
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran for 1.5 h;
Stage #3: With hydrogenchloride In water
To a solution of monodispersed tetraethylene glycol (51.5 g, 0.27 mol) in THF (1L) was added potassium t-butoxide (14.8 g, 0.13 mol, small portions over 30 min). The reaction mixture was then stirred for 1 h and then 9 (29.15 g, 0.12 mol) dissolved in THF (90 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed CH2Cl2, 200 mL) and evaporated to dryness. The oil was then dissolved in HCl (250 mL, 1 N) and washed with ethyl acetate (250 mL) to remove excess 9. Additional washings of ethyl acetate (125 mL) may be required to remove remaining 9. The aqueous phase was washed repetitively with CH2Cl2 (125 mL volumes) until most of the compound 18 has been removed from the aqueous phase. The first extraction will contain 9, 10, and dicoupled side product and should be back extracted with HCl (125 mL, 1N). The organic layers were combined and evaporated to dryness. The resultant oil was then dissolved in CH2Cl2 (100 mL) and washed repetitively with H2O (50 mL volumes) until 10 was removed. The aqueous fractions were combined, total volume 500 mL, and NaCl was added until the solution became cloudy and then was washed with CH2Cl2 (2.x.500 mL). The organic layers were combined, dried MgSO4, and evaporated to dryness to afford the monodispersed compound 10 as an oil (16.9 g, 41percent yield). It may be desirable to repeat one or more steps of the purification procedure to ensure high purity.
Reference: [1] Patent: US2003/228275, 2003, A1, . Location in patent: Page 40
[2] Patent: US2003/228275, 2003, A1, . Location in patent: Page 42
[3] Patent: US2003/229009, 2003, A1, . Location in patent: Page 38
  • 2
  • [ 112-35-6 ]
  • [ 4437-01-8 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; for 12 h; Inert atmosphere
Stage #3: With sulfuric acid; water In tetrahydrofuran for 3 h; Inert atmosphere; Reflux
General procedure: (Using the synthesis of M-PEG 7 as an example). Under the atmosphere of N2, to a suspension of NaH (1.0 g, 60percent dispersed in mineral oil, 25.0 mmol) in THF (60 mL) at 0 was added a solution of M-PEG 5 (2.0 g, 16.6 mmol) in THF (20 mL). After the addition, the stirring mixture was warmed to rt and stirred for 30 min. Then, a solution of macrocyclic sulfate 8 (5.1 g, 20.0 mmol) in THF (20 mL) was added. The resulting mixture was stirred for 12 h at rt, and concentrated under vacuum. The resulting residue was dissolved in water (50 mL), and washed with CH2Cl2. The aqueous layer was concentrated and then dissolved in THF (100 mL). Then, water (0.6 mL, 33.3 mmol) and H2SO4 (0.4 mL, 8.4 mmol) were added to the reaction mixture and the resulting mixture was refluxed for 3 h. The reaction was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2. The organic layers were dried over anhydrous Na2SO4, concentrated under vacuum, and purified by flash chromatography on silica gel (CH2Cl2/MeOH = 20/1) to give M-OEG 7 as clear oil (4.3 g, 88percent yield).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 22, p. 3502 - 3505
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 30, p. 4461 - 4468
  • 3
  • [ 74654-05-0 ]
  • [ 68999-61-1 ]
  • [ 4437-01-8 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: at 20℃; for 3.5 h;
Stage #2: With hydrogenchloride In water
To a stirred solution of monodispersed tetraethylene glycol (35.7 mmol) in dry DMF (25.7 ML), under N2 was added in portion a 60percent dispersion of NaH in mineral oil, and the mixture was stirred at room temperature for 1 hour.To the resulting sodium salt of the tetraethylene glycol was added a solution of monodispersed mesylate 29 (23.36) in dry DMF (4 ml) in a single portion, and the mixture was stirred at room temperature for 3.5 hours.Progress of the reaction was monitored by TLC (12percent CH3OH-CHCl3).The reaction mixture was diluted with an equal amount of 1N HCl, and extracted with ethyl acetate (2*20 ml) and discarded.Extraction of aqueous solution and work-up gave monodispersed heptaethylene glycol monomethyl ether 30 (82-84percent yield). Oil; Rf 0.46 (methanol:chloroform=3:22); MS m/z calc'd for C15H32O8 340.21 (M++1), found 341.2.
Reference: [1] Patent: US2003/229009, 2003, A1, . Location in patent: Page 41
  • 4
  • [ 2615-15-8 ]
  • [ 6482-24-2 ]
  • [ 4437-01-8 ]
YieldReaction ConditionsOperation in experiment
41% With sodium hydride In tetrahydrofuran at 20℃; for 2 h; To a solution of hexa(ethylene glycol)(10 g, 35 mmole) and 2-bromoethyl methyl ether (4.9 g, 35 mmole) in THF (100 mL) was slowly added sodium hydride (2.55 g, 106 mmole). The solution was stirred at room temperature for two hours. HPLC indicated that mPEG7-OH was formed in about 54percent yield. The reaction was then stopped by the addition of diluted hydrochloride acid to destroy excess sodium hydride. All solvents were removed using a rotary evaporator to give a brown sticky liquid. Pure mPEG7-OH was obtained as a colorless liquid (4.9 g, 41percent isolated yield) by using semi-preparative HPLC (20 cm.x.4 cm, C18 column, acetonitrile and water as mobile phases). 1H NMR (CDCl3): 2.57 ppm (triplet, 1 H, OH); 3.38 ppm (singlet, 3 H, CH3O); 3.62 ppm (multiplet, 30 H, OCH2CH2).
Reference: [1] Patent: US2005/136031, 2005, A1, . Location in patent: Page/Page column 25
  • 5
  • [ 112-60-7 ]
  • [ 4437-01-8 ]
Reference: [1] Patent: US2003/87808, 2003, A1,
[2] Patent: US2003/69170, 2003, A1,
[3] Patent: US2004/38866, 2004, A1,
[4] Patent: US2003/228652, 2003, A1,
[5] Patent: US6867183, 2005, B2,
[6] Patent: WO2018/96464, 2018, A1,
[7] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 22, p. 3502 - 3505
  • 6
  • [ 112-60-7 ]
  • [ 4437-01-8 ]
YieldReaction ConditionsOperation in experiment
41% With sodium chloride In tetrahydrofuran; hydrogenchloride; dichloromethane; ethyl acetate Example 20
Heptaethylene glycol monomethyl ether (25)
To a solution of non-polydispersed tetraethylene glycol (51.5 g, 0.27 mol) in THF (1L) was added potassium t-butoxide (14.8 g, 0.13 mol, small portions over -30 min).
The reaction mixture was then stirred for lh and then 24 (29.15 g, 0.12 mol) dissolved in THF (90 mL) was added dropwise and the reaction mixture was stirred overnight.
The crude reaction mixture was filtered through Celite (washed CH2Cl2, ~200 mL) and evaporated to dryness.
The oil was then dissolved in HCl (250 mL, 1 N) and washed with ethyl acetate (250 mL) to remove excess 24.
Additional washings of ethyl acetate (125 mL) may be required to remove remaining 24.
The aqueous phase was washed repetitively with CH2Cl2 (125 mL volumes) until most of the 25 has been removed from the aqueous phase.
The first extraction will contain 24, 25, and dicoupled side product and should be back extracted with HCl (125 mL, 1N).
The organic layers were combined and evaporated to dryness.
The resultant oil was then dissolved in CH2Cl2 (100 mL) and washed repetitively with H2O (50 mL volumes) until 25 was removed.
The aqueous fractions were combined, total volume 500 mL, and NaCl was added until the solution became cloudy and then was washed with CH2Cl2 (2*500 mL).
The organic layers were combined, dried MgSO4, and evaporated to dryness to afford a the non-polydispersed title compound as an oil (16.9 g, 41percent yield).
It may be desirable to repeat one or more steps of the purification procedure to ensure high purity.
41% With sodium chloride In tetrahydrofuran; hydrogenchloride; dichloromethane; ethyl acetate Example 20
Heptaethylene Glycol Monomethyl Ether (25)
To a solution of non-polydispersed tetraethylene glycol (51.5 g, 0.27 mol) in THF (1L) was added potassium t-butoxide (14.8 g, 0.13 mol, small portions over ~30 min).
The reaction mixture was then stirred for lh and then 24 (29.15 g, 0.12 mol) dissolved in THF (90 mL) was added dropwise and the reaction mixture was stirred overnight.
The crude reaction mixture was filtered through Celite (washed CH2Cl2,~200 mL) and evaporated to dryness.
The oil was then dissolved in HCl (250 mL, 1 N) and washed with ethyl acetate (250 mL) to remove excess 24.
Additional washings of ethyl acetate (125 mL) may be required to remove remaining 24.
The aqueous phase was washed repetitively with CH2Cl2 (125 mL volumes) until most of the 25 has been removed from the aqueous phase.
The first extraction will contain 24, 25, and dicoupled side product and should be back extracted with HCl (125 mL, 1N).
The organic layers were combined and evaporated to dryness.
The resultant oil was then dissolved in CH2Cl2 (100 mL) and washed repetitively with H2O (50 mL volumes) until 25 was removed.
The aqueous fractions were combined, total volume 500 mL, and NaCl was added until the solution became cloudy and then was washed with CH2Cl2 (2*500 mL).
The organic layers were combined, dried MgSO4, and evaporated to dryness to afford a the non-polydispersed title compound as an oil (16.9 g, 41percent yield).
It may be desirable to repeat one or more steps of the purification procedure to ensure high purity.
Reference: [1] Patent: US2003/27748, 2003, A1,
[2] Patent: US2003/27995, 2003, A1,
  • 7
  • [ 112-60-7 ]
  • [ 62921-74-8 ]
  • [ 4437-01-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 6, p. 1700 - 1707
  • 8
  • [ 112-60-7 ]
  • [ 52995-76-3 ]
  • [ 4437-01-8 ]
Reference: [1] Liebigs Annalen der Chemie, 1980, # 6, p. 858 - 862
[2] Journal of Mass Spectrometry, 2002, vol. 37, # 7, p. 699 - 708
  • 9
  • [ 112-35-6 ]
  • [ 4437-01-8 ]
Reference: [1] Journal of Mass Spectrometry, 2002, vol. 37, # 7, p. 699 - 708
[2] Patent: CN105732338, 2016, A,
[3] Patent: WO2018/96464, 2018, A1,
  • 10
  • [ 74654-05-0 ]
  • [ 4437-01-8 ]
Reference: [1] Patent: WO2018/96464, 2018, A1,
  • 11
  • [ 1134159-70-8 ]
  • [ 4437-01-8 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 3, p. 875 - 881
  • 12
  • [ 5197-62-6 ]
  • [ 4437-01-8 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 3, p. 875 - 881
  • 13
  • [ 85539-28-2 ]
  • [ 4437-01-8 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 3, p. 875 - 881
  • 14
  • [ 86259-87-2 ]
  • [ 4437-01-8 ]
Reference: [1] Patent: WO2018/96464, 2018, A1,
  • 15
  • [ 23778-52-1 ]
  • [ 4437-01-8 ]
Reference: [1] Patent: US2798873, 1953, ,
  • 16
  • [ 4437-01-8 ]
  • [ 854601-70-0 ]
Reference: [1] Patent: WO2018/96464, 2018, A1,
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