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[ CAS No. 3056-18-6 ] {[proInfo.proName]}

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Chemical Structure| 3056-18-6
Chemical Structure| 3056-18-6
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Product Details of [ 3056-18-6 ]

CAS No. :3056-18-6 MDL No. :MFCD02093101
Formula : C16H16Cl2N4O7 Boiling Point : -
Linear Structure Formula :- InChI Key :PYXZXWLFAMZVPY-SDBHATRESA-N
M.W : 447.23 Pubchem ID :10253027
Synonyms :
2,6-Dichloro-2',3',5'-triacetyl-purine riboside;2,6-Dichloro-9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)purine

Calculated chemistry of [ 3056-18-6 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.5
Num. rotatable bonds : 8
Num. H-bond acceptors : 10.0
Num. H-bond donors : 0.0
Molar Refractivity : 97.5
TPSA : 131.73 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) : -6.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.19
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 1.13
Log Po/w (MLOGP) : -0.1
Log Po/w (SILICOS-IT) : 0.95
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.18
Solubility : 0.0296 mg/ml ; 0.0000662 mol/l
Class : Moderately soluble
Log S (Ali) : -5.39
Solubility : 0.00183 mg/ml ; 0.00000408 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.434 mg/ml ; 0.000971 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.37

Safety of [ 3056-18-6 ]

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 [ 3056-18-6 ]

* 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 [ 3056-18-6 ]
  • Downstream synthetic route of [ 3056-18-6 ]

[ 3056-18-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 16321-99-6 ]
  • [ 5987-73-5 ]
  • [ 3056-18-6 ]
  • [ 40896-58-0 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 666 - 669
  • 2
  • [ 16321-99-6 ]
  • [ 3056-18-6 ]
YieldReaction ConditionsOperation in experiment
82% With chloro-trimethyl-silane; isopentyl nitrite In dichloromethane at 0 - 5℃; for 1 h; Isoamyl nitrite (165 g, 1.41 mol) was dissolved in methylene chloride (500 mL) and then stirred at 0~5 ° C.Trimethylchlorosilane (76 g, 0.70 mol) was added,Then a solution of compound IV (100 g, 0.234 mol) in DCM was added(500mL) was added dropwise to the above mother liquor, after the addition was complete,Continue to stir the reaction at this temperature for 1 hour,The reaction was completed, saturated sodium sulfite solution, liquid separation,The separated organic phase was washed with aqueous sodium bicarbonate,Washed with saturated saline, and dried over anhydrous sodium sulfate, filtered,The mixture was concentrated under reduced pressure until no solution was distilled off. The residue was recrystallized by adding dichloromethane (100 mL) and n-heptane (350 mL)The resulting yellow solid, Compound V (2,6-dichloro-9- (2 ', 3', 5'-tri-O-acetyl-β-D-ribofuranosyl) purine) 86g, molar yield of 82percent.
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 666 - 669
[2] Canadian Journal of Chemistry, 1981, vol. 59, # 17, p. 2608 - 2611
[3] Patent: CN106397516, 2017, A, . Location in patent: Paragraph 0029; 0030; 0080; 0081; 0082; 0083
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 24, p. 4557 - 4561
[5] Journal of Organic Chemistry, 2002, vol. 67, # 19, p. 6788 - 6796
[6] Synthesis, 1982, # 8, p. 670 - 672
[7] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 4, p. 525 - 531
[8] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 24, p. 3085 - 3090
[9] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 85 - 87
[10] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 4, p. 403 - 406
[11] Tetrahedron Letters, 2012, vol. 53, # 11, p. 1358 - 1362
[12] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 2, p. 436 - 447
  • 3
  • [ 5451-40-1 ]
  • [ 13035-61-5 ]
  • [ 3056-18-6 ]
YieldReaction ConditionsOperation in experiment
79% With silica gel 60 In ethyl acetate for 0.5 h; Microwave irradiation 2,6-Dichloropurine (23) (190 mg, 1 mmol) and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (318 mg, 1 mmol) were dissolved in EtOAc, then 500 mg of silica gel 60 (200-400 mesh) was added. The mixture was concentrated in vacuo and the dry residue was irradiated for 30 min in a domestic microwave oven (120 W). The residue was purified by flash chromatography on silica gel (EtOAc-hexane, 1:2) to yield 24 as yellowish viscous oil (350 mg, 79percent). 1H NMR (CDCl3) δ2.10 (s, 3H, CH3), 2.14 (s, 3H, CH3), 2.17 (s, 3H, CH3), 4.42 (d, 2H, CH2-5’), 4.50 (q, 1H, H-4’), 5.59 (t, 1H, H-3’), 5.81 (t, 1H, H-2’), 6.24 (d, 1H, H-1’), 8.33 (s, 1H, H-8). 13C NMR (DMSO-d6) δ 20.53, 20.70, 20.95 (3xCH3), 63.06 (CH2-5′), 70.72 (CH-4’), 73.42 (CH-3’), 81.02 (CH-2’), 86.74 (CH-1’), 131.56 (C-5), 144.10 (C-8), 152.44 (C-6), 152.79 (C-4), 153.55 (C-2), 169.56, 169.74, 170.39 (3xCO). MS (ESI+) m/e: 447.5 (percent100) (M), 449.9 (percent50) (M+2), 451.6 (percent17) (M+4).
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 1, p. 196 - 197
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 3, p. 235 - 239
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 14, p. 6467 - 6477
[4] Nucleosides, nucleotides and nucleic acids, 2002, vol. 21, # 1, p. 73 - 78
  • 4
  • [ 79999-38-5 ]
  • [ 3056-18-6 ]
Reference: [1] Canadian Journal of Chemistry, 1981, vol. 59, # 17, p. 2601 - 2607
[2] Journal of Organic Chemistry, 2010, vol. 75, # 14, p. 4880 - 4883
  • 5
  • [ 118-00-3 ]
  • [ 3056-18-6 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 85 - 87
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 24, p. 3085 - 3090
[3] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 4, p. 525 - 531
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 2, p. 436 - 447
  • 6
  • [ 6979-94-8 ]
  • [ 3056-18-6 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 85 - 87
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 24, p. 3085 - 3090
[3] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 4, p. 525 - 531
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 2, p. 436 - 447
  • 7
  • [ 30571-54-1 ]
  • [ 5451-40-1 ]
  • [ 3056-18-6 ]
Reference: [1] Patent: US5256650, 1993, A,
  • 8
  • [ 16321-99-6 ]
  • [ 5987-73-5 ]
  • [ 3056-18-6 ]
  • [ 40896-58-0 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 666 - 669
  • 9
  • [ 5383-06-2 ]
  • [ 3056-18-6 ]
Reference: [1] Canadian Journal of Chemistry, 1981, vol. 59, # 17, p. 2601 - 2607
  • 10
  • [ 79999-37-4 ]
  • [ 3056-18-6 ]
Reference: [1] Canadian Journal of Chemistry, 1981, vol. 59, # 17, p. 2601 - 2607
  • 11
  • [ 58-61-7 ]
  • [ 3056-18-6 ]
Reference: [1] Canadian Journal of Chemistry, 1981, vol. 59, # 17, p. 2601 - 2607
  • 12
  • [ 3056-18-6 ]
  • [ 13276-52-3 ]
YieldReaction ConditionsOperation in experiment
85% With acetyl chloride In methanol at 0 - 10℃; for 1.5 h; Inert atmosphere Under a nitrogen atmosphere, to a three-necked flask equipped with a dropping funnel, 450 ml of all-acetyl protected 2,6-dichloropurine (0.1 mole) and anhydrous methanol were added,Stir until the system is completely clear, cooled to 0-10 , acetyl chloride (1.2mol) was slowly added dropwise, the addition was complete, the reaction was continued for 1.5 hours, TLC detection reaction was complete;To the reaction system, solid potassium carbonate was added in portions until pH = 7-8, filtered, the filtrate was concentrated to dryness, water was added,Extracted three times with 250 ml of ethyl acetate, the combined extracts were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated to dryness.Recrystallization by adding 140 ml of isopropanol gave 27.3 g of 2,6-dichloropurine as a white solid in 85percent yield,
Reference: [1] Patent: CN105085595, 2017, B, . Location in patent: Paragraph 0015; 0016; 0017; 0018
  • 13
  • [ 3056-18-6 ]
  • [ 163706-58-9 ]
Reference: [1] Patent: CN106397516, 2017, A,
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