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[ CAS No. 86357-14-4 ] {[proInfo.proName]}

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Chemical Structure| 86357-14-4
Chemical Structure| 86357-14-4
Structure of 86357-14-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 86357-14-4 ]

CAS No. :86357-14-4 MDL No. :MFCD08457700
Formula : C15H19N5O7 Boiling Point : -
Linear Structure Formula :- InChI Key :PEZKHGVZZSQDPY-UHFFFAOYSA-N
M.W : 381.34 Pubchem ID :135427290
Synonyms :

Calculated chemistry of [ 86357-14-4 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.47
Num. rotatable bonds : 11
Num. H-bond acceptors : 9.0
Num. H-bond donors : 2.0
Molar Refractivity : 91.03
TPSA : 154.5 Ų

Pharmacokinetics

GI absorption : Low
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) : -9.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.69
Log Po/w (XLOGP3) : -0.89
Log Po/w (WLOGP) : -0.8
Log Po/w (MLOGP) : -0.71
Log Po/w (SILICOS-IT) : 0.31
Consensus Log Po/w : -0.28

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 2.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.16
Solubility : 26.1 mg/ml ; 0.0685 mol/l
Class : Very soluble
Log S (Ali) : -1.87
Solubility : 5.12 mg/ml ; 0.0134 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.73
Solubility : 0.71 mg/ml ; 0.00186 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.2

Safety of [ 86357-14-4 ]

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

Application In Synthesis of [ 86357-14-4 ]

* 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 [ 86357-14-4 ]
  • Downstream synthetic route of [ 86357-14-4 ]

[ 86357-14-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 86357-14-4 ]
  • [ 82410-32-0 ]
YieldReaction ConditionsOperation in experiment
87% With acetic acid In water; methylamine Example 8
Preparation of 9-(1,3-dihydroxy-2-propoxymethyl)guanine 12 and 7-(1,3-dihydroxy-2-propoxymethyl)guanine 11
Compound 9 (8.0 g) was dissolved in 100 ml of aqueous methylamine (40percent) and gently refluxed for 1.5 hours, and then was evaporated to dryness to give a white solid.
The solid was crystallized from 50 ml of water and 10 drops of acetic acid (to neutralize amine and remove the color) to give a white crystalline product 12 (4.63 g, 87percent).
mp>300° (dec.); Rf 0.62 (CH3 OH:CHCl3 =1:1); UV (H2 O) pH7 λmax 251.5 (ε 10180), 272.0 (sh, ε 7500), pH2 λmax 253.5 (ε9840), pH 11 λmax 265.6 (ε 8060); 1 H NMR (DMSO-d6) δ 10.64 (s, 1H, AcNH, D2 O exchangeable), 7.80 (s, 1H, 8-H), 6.49 (s, 2H, NH2 D2 O exchangeable), 5.43 (s, 2H, 1'-H), 4.61 (t, 2H, OH, D2 O exchangeable), 3.55-3.28 (m, 5H, 4'-H, 5'-H, 3'-H).
82.8% at 70℃; for 0.5 h; Microwave irradiation In the second step, the above-mentioned triacetyl ganciclovir compound (2) 67.1 g and 10percent potassium hydroxide solution 200 g are put into a microwave reactor.The temperature was raised to 70 ° C for 0.5 hour, cooled to room temperature, sulfuric acid was added to adjust the pH to neutrality, 3.3 g of activated carbon was added, and then dissolved.The mixture was decolorized by reflux at elevated temperature for 1 hour, filtered, and the filtrate was cooled to 10 ° C for crystallization.Filtration and drying gave 37.5 g of crude ganciclovir, the yield was 84.2percent, and the purity was 97.1percent. In the third step, 37.5 g of crude ganciclovir and 187 g of DMF were added to the reaction flask, and the mixture was heated to 90 ° C until stirred.Then cooled to 40 ° C, added 561g of methanol, and continued to cool to 20 ° C for 5 hours.Filtration, methanol washing, drying to obtain pure ganciclovir 31.0g, yield 82.8percent, purity 99.0percent,
Reference: [1] Synthesis, 1999, # 4, p. 625 - 628
[2] Patent: US5583225, 1996, A,
[3] Patent: CN108467396, 2018, A, . Location in patent: Paragraph 0030; 0032; 0034; 0035; 0036; 0038; 0039; 0040
[4] Patent: US4816447, 1989, A,
  • 2
  • [ 86357-14-4 ]
  • [ 88110-89-8 ]
Reference: [1] Patent: EP1837336, 2007, A1, . Location in patent: Page/Page column 10-11
[2] Patent: EP1837336, 2007, A1, . Location in patent: Page/Page column 11
[3] Patent: EP1837336, 2007, A1, . Location in patent: Page/Page column 11
[4] Patent: EP1837336, 2007, A1, . Location in patent: Page/Page column 11
[5] Patent: US2007/225305, 2007, A1, . Location in patent: Page/Page column 7
[6] Patent: US2007/225305, 2007, A1, . Location in patent: Page/Page column 7
[7] Patent: US2007/225305, 2007, A1, . Location in patent: Page/Page column 8
[8] Patent: US2007/225305, 2007, A1, . Location in patent: Page/Page column 7-8
  • 3
  • [ 86357-13-3 ]
  • [ 3056-33-5 ]
  • [ 86357-14-4 ]
YieldReaction ConditionsOperation in experiment
85.3% With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 100℃; for 10 h; Microwave irradiation In the first step, 20.0-diacetylguanine 50.0 g (0.21 mol, 1.0 eq), 1,3-diacetoxy-2-(acetoxymethoxy)propane 104.2 g (0.42 mol, 2.0 eq ),3.0 g (0.021 mol, 0.1 eq) of boron trifluoride etherate and 200 g of N,N-dimethylformamide were placed in a microwave reactor, and the mixture was heated to 100 ° C for 10 hours.The solvent was distilled off under reduced pressure, and the mixture was cooled to room temperature. 450 g of ethyl acetate was added and refluxed for 1 hour, and the temperature was lowered to 0 to 5 ° C for 1 hour.After suction filtration and drying, the triacetyl ganciclovir compound (2) 68.3 g, the yield was 85.3percent,The purity was 95.6percent, and the compound (3) was 3.1percent.
Reference: [1] Patent: CN108467396, 2018, A, . Location in patent: Paragraph 0030; 0031; 0036; 0037; 0040; 0041; 0044; 0045
  • 4
  • [ 86357-13-3 ]
  • [ 3056-33-5 ]
  • [ 86357-14-4 ]
Reference: [1] Patent: WO2004/48380, 2004, A1, . Location in patent: Page 6
[2] Patent: WO2004/48380, 2004, A1, . Location in patent: Page 7
  • 5
  • [ 86357-13-3 ]
  • [ 86357-17-7 ]
  • [ 86357-14-4 ]
YieldReaction ConditionsOperation in experiment
46.7% With phosphoric acid In chloroform; N,N-dimethyl-formamide Example 7
Preparation of 9-[2-Acetoxy-1-(acetoxymethyl)ethoxy]methyl}-2-acetamidopurine-6-one (9) and 7-[2-acetoxy-1-(acetoxymethyl)ethoxy]methyl}-2-acetaminopurine-6-one (10)
A mixture of diacetylguanine (10.575 g, 45 mmol), 2-acetoxymethoxy-1,3-diacetoxypropane (22.32 g, 90 mmol) and phosphoric acid (0.3 ml) in DMF (45 ml) was heated for three hours at 120° (oil bath 135°) with stirring.
The suspension gradually became homogeneous.
When TLC indicated the reaction was complete, the reaction solution was evaporated in vacuo to remove solvents yielding a dark-brown syrup.
The syrup was dissolved in small amount of CHCl3 and applied to a column (silica gel 60, φ4*27 cm), eluted with CH3 OH:CHCl3 (0-3percent) to give 9 (8.0 g, 46.7percent) and 10 (5.1 g, 29.8percent).
Compound 9:
mp 165°-7° (ethyl acetate); Rf 0.49 (CH3 OH--CHCl3 =1:9); UV (CH3 OH) λmax 254.5, 278.0 (sh); 1 H NMR (DMSO-d6) δ 12.07, 11.78 (NH, s, 2H, D2 O exchangeable), 8.14 (s, H, 8-H), 5.53 (s, 2H, OCH2 N), 4.11-3.94 (m, 5H, (OCH2 CH)2 CH), 2.18 (s, 3H, AcN), 1.88 (s, 6H, AcO).
Compound 10:
mp 176°-178°; Rf 0.61 (CH3 OH:CHCl3 =1:9); UV (CH3 OH) λmax 261.5 nm; 1 H NMR (DMSO-d6) δ 12.18, 11.63 (s, 2H, NH, D2 O exchangeable), 8.38 (s, 1H, 8-H), 5.73 (s, 2H, OCH2 N), 4.14-3.92 (m, 5H, (OCH2 CH)2 CH), 2.17 (s, 3H, AcN), 1.88 (s, 6H, AcO).
Reference: [1] Patent: US5583225, 1996, A,
  • 6
  • [ 82410-32-0 ]
  • [ 108-24-7 ]
  • [ 86357-14-4 ]
YieldReaction ConditionsOperation in experiment
80% for 6 h; Reflux Ganciclovir (1.0 g, 4.0 mmol), acetic anhydride (5.0 ml, 53 mmol), and pyridine (10.0 ml) were heated together, under reflux, for 6 hours. Initially, the reaction mixture was not homogeneous but once reaction completed, all were in the solution. The reaction was cooled, treated with methanol (5.0 ml), stirred for 30 minutes at 25° C., and then concentrated under reduced pressure. The crude gummy product was purified by silica gel column chromatography using 4-6percent methanol/ dichloromethane 4 to provide tri-acetylated ganciclovir, 2 (1.2 g, 3.14 mmol, yield 80percent) as a colorless powdered. 1H NMR (CDCl3, 400 MHz): δ 12.02 (s, 1H), 9.49 (s, 1H), 7.84 (s, 1H), 5.55 (s, 2H), 4.19 (t, J=4.0 Hz, 4H), 4.12 (m, 1H), 2.35 (s, 3H), 2.05 (s, 6H). ESI-LC/MS: Expected [M+H]+ for C15H19N5O7 is 382.13, found m/z: 382.37 [M+H]+.
Reference: [1] Patent: US2017/50967, 2017, A1, . Location in patent: Paragraph 0122
  • 7
  • [ 86357-13-3 ]
  • [ 86357-17-7 ]
  • [ 86357-14-4 ]
  • [ 13035-61-5 ]
Reference: [1] Synthesis, 1999, # 4, p. 625 - 628
  • 8
  • [ 86357-17-7 ]
  • [ 86357-14-4 ]
Reference: [1] Synthesis, 1999, # 4, p. 625 - 628
  • 9
  • [ 86357-13-3 ]
  • [ 86357-14-4 ]
Reference: [1] Synthesis, 1999, # 4, p. 625 - 628
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