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[ CAS No. 1118567-05-7 ] {[proInfo.proName]}

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Chemical Structure| 1118567-05-7
Chemical Structure| 1118567-05-7
Structure of 1118567-05-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1118567-05-7 ]

CAS No. :1118567-05-7 MDL No. :MFCD28100944
Formula : C24H29ClO7 Boiling Point : -
Linear Structure Formula :- InChI Key :BTCRKOKVYTVOLU-SJSRKZJXSA-N
M.W : 464.94 Pubchem ID :25195624
Synonyms :
EGT-1442;THR-1442;EGT-0001442

Calculated chemistry of [ 1118567-05-7 ]

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.5
Num. rotatable bonds : 9
Num. H-bond acceptors : 7.0
Num. H-bond donors : 4.0
Molar Refractivity : 118.22
TPSA : 108.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.99
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 1.62
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 3.16
Consensus Log Po/w : 2.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.91
Solubility : 0.057 mg/ml ; 0.000123 mol/l
Class : Soluble
Log S (Ali) : -4.31
Solubility : 0.0227 mg/ml ; 0.0000487 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.77
Solubility : 0.00797 mg/ml ; 0.0000171 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.9

Safety of [ 1118567-05-7 ]

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 [ 1118567-05-7 ]

* 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 [ 1118567-05-7 ]
  • Downstream synthetic route of [ 1118567-05-7 ]

[ 1118567-05-7 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 1459754-30-3 ]
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YieldReaction ConditionsOperation in experiment
90% With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at -25 - -20℃; for 4 h; Inert atmosphere; Large scale Example 5 Preparation of ((2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-(2-Cyclopropoxyethoxy)Benzyl)Phenyl)-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-3,4,5-triol [0236] This example describes preparation of (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol by reduction of the anomeric OMe and/or OH. (3R,4S,5S,6R)-2-(4-Chloro-3-(4-(2-Cyclopropoxyethoxy)Benzyl)Phenyl)-6-(Hydroxymethyl)-2-Methoxytetrahydro-2H-Pyran-3,4,5-Triol Solution [0237] A 30 L glass reactor equipped with a thermometer was charged with crude (3R,4S,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (2.7 kg), DCM (5.4 kg) and acetonitrile (3.2 kg), and the mixture was magnetically stirred until all the solids dissolved under nitrogen sparging. [0238] Triethylsilane Solution: [0239] BF3.Et2O (2.34 kg) was added to a cold (−21 to −15° C.) solution of triethysilane (2.55 kg) dichloromethane (5.4 kg) and acetonitrile (3.2 kg) under nitrogen. [0240] The (3R,4S,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol solution was added to the cold triethylsilane solution at such a rate to maintain the temperature between −20 and −25° C. (3 h). [0241] The reaction mixture was stirred for another 4 h at −22 to −25° C. and then quenched by addition of an aqueous solution of sodium bicarbonate (7.4percent w/w, 18.3 kg) while keeping the internal temperature below −10° C. Solid sodium bicarbonate (1.35 kg) was added to adjust the pH to 7.5. The solvents were removed under reduced pressure (temperature below 40° C.). The residue was partitioned between ethyl acetate (18 kg) and water (9.2 kg). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×9 kg). The combined organic layers were washed with brine (2×9 kg) and the solvents were removed under reduced pressure at the temperature below 40° C. until the condensation almost stop Anhydrous ethanol (9 kg) was added and concentrated to give the crude product of the title compound (2.5 kg, 90percent yield, 90.8percent HPLC purity, HPLC-0001) as foamy solid.
70% With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at -25 - -20℃; Inert atmosphere General procedure: To a solution of 16b (2.1 g, 4.2 mmol) in dichloromethane (10.5 mL) and acetonitrile (10.5 mL) at –25 °C under argon was added triethylsilane (2.7 mL, 16.8 mmol). Then boron trifluoride etherate (1.6 mL, 12.6 mmol) was added while maintaining the reaction temperature below –20 °C, and the reaction mixture was stirred for another 4 h at –25 to –20 °C. The reaction was quenched by addition of 5percent sodium bicarbonate until a pH of 7.5 was obtained. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2 × 50 mL). The combined organic phases were washed with water (50 mL), brine (50 mL) and dried over anhydrous sodium sulfate. The sample was concentrated under reduced pressure to give product crude 7b as a light yellow solid (1.82 g, 92percent yield; HPLC purity: 88.3percent).
Reference: [1] Patent: US2013/267694, 2013, A1, . Location in patent: Paragraph 0236; 0237; 0238; 0239; 0240; 0241
[2] Tetrahedron Letters, 2016, vol. 57, # 42, p. 4684 - 4687
[3] Patent: WO2013/152476, 2013, A1, . Location in patent: Paragraph 0206; 0207; 0208; 0209; 0210
[4] Patent: WO2013/152654, 2013, A1, . Location in patent: Paragraph 0212-0216
  • 2
  • [ 1118567-46-6 ]
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Reference: [1] Patent: WO2010/22313, 2010, A2, . Location in patent: Page/Page column 47-50
[2] Patent: WO2011/153712, 2011, A1, . Location in patent: Page/Page column 29; 32-33
[3] Patent: WO2011/153953, 2011, A1, . Location in patent: Page/Page column 30; 33; 34
  • 3
  • [ 864070-37-1 ]
  • [ 862728-59-4 ]
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Reference: [1] Patent: WO2009/26537, 2009, A1, . Location in patent: Page/Page column 72
  • 4
  • [ 18742-02-4 ]
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Reference: [1] Patent: WO2009/26537, 2009, A1,
  • 5
  • [ 21739-92-4 ]
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Reference: [1] Patent: WO2009/26537, 2009, A1,
  • 6
  • [ 1459754-30-3 ]
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Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 42, p. 4684 - 4687
  • 7
  • [ 461432-23-5 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4465 - 4470
[2] Patent: WO2009/26537, 2009, A1,
  • 8
  • [ 864070-18-8 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4465 - 4470
  • 9
  • [ 1118567-45-5 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4465 - 4470
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  • [ 1118566-50-9 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4465 - 4470
  • 11
  • [ 1118566-69-0 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4465 - 4470
  • 12
  • [ 90-80-2 ]
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Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 42, p. 4684 - 4687
  • 13
  • [ 32469-28-6 ]
  • [ 1118567-05-7 ]
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 42, p. 4684 - 4687
  • 14
  • [ 461432-22-4 ]
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Reference: [1] Patent: WO2009/26537, 2009, A1,
  • 15
  • [ 1118566-45-2 ]
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Reference: [1] Patent: WO2009/26537, 2009, A1,
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  • [ 461432-24-6 ]
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Reference: [1] Patent: WO2009/26537, 2009, A1,
  • 17
  • [ 20117-44-6 ]
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Reference: [1] Patent: WO2009/26537, 2009, A1,
  • 18
  • [ 21900-52-7 ]
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Reference: [1] Patent: WO2009/26537, 2009, A1,
  • 19
  • [ 90-80-2 ]
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Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 42, p. 4684 - 4687
  • 20
  • [ 32469-28-6 ]
  • [ 1118567-05-7 ]
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 42, p. 4684 - 4687
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