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[ CAS No. 5987-73-5 ] {[proInfo.proName]}

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Chemical Structure| 5987-73-5
Chemical Structure| 5987-73-5
Structure of 5987-73-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5987-73-5 ]

CAS No. :5987-73-5 MDL No. :MFCD09841351
Formula : C16H17ClN4O7 Boiling Point : -
Linear Structure Formula :- InChI Key :INOTYVPMBNDAFK-XNIJJKJLSA-N
M.W : 412.78 Pubchem ID :11825800
Synonyms :

Calculated chemistry of [ 5987-73-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 28
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 : 92.49
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) : -7.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.81
Log Po/w (XLOGP3) : 1.99
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : -0.2
Log Po/w (SILICOS-IT) : 0.28
Consensus Log Po/w : 1.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.36
Solubility : 0.179 mg/ml ; 0.000434 mol/l
Class : Soluble
Log S (Ali) : -4.38
Solubility : 0.0171 mg/ml ; 0.0000414 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.43
Solubility : 1.53 mg/ml ; 0.00372 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.32

Safety of [ 5987-73-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5987-73-5 ]

* 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 [ 5987-73-5 ]
  • Downstream synthetic route of [ 5987-73-5 ]

[ 5987-73-5 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 5987-73-5 ]
  • [ 39824-26-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 6, p. 695 - 698
  • 2
  • [ 5987-73-5 ]
  • [ 16645-06-0 ]
  • [ 31199-61-8 ]
  • [ 3181-38-2 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 1887 - 1894
  • 3
  • [ 3181-38-2 ]
  • [ 5987-73-5 ]
YieldReaction ConditionsOperation in experiment
100% With N-benzyl-N,N,N-triethylammonium chloride; <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate In acetonitrile at 70℃; for 2 h; 2,3,5-Tri-O-acetylinosine [4] (5.00g, 12.68 mmol, 1.00 equiv), benzyltriethylammonium chloride (5.77 g, 25.36 mmol, 2.00 equiv) andN,N-dimethylaniline (1.8 mL, 13.94 mmol, 1.10 equiv) were dissolved in 50 mL dry acetonitrile. Theflask was placed on a preheated oil bath (70 °C), POCl3 (5.9 mL, 63.40 mmol, 5.00 equiv) was addedslowly and the reaction mixture was stirred for 2 h at the same temperature. After that, the solvent andexcess POCl3 were removed under reduced pressure (high vacuum, 70 °C). The residue was pouredon a CHCl3/ice-mixture and the solution was stirred for 20 min. The organic phase was separated andthe aqueous phase was extracted 3 times with CHCl3. The organic phases were combined and washedwith a 5 percent NaHCO3 solution until the aqueous layer showed a slightly basic reaction. Subsequentlythe organic phase was separated, dried with MgSO4 and the solvent was removed under reducedpressure. Purification by silica gel chromatography (EtOAc) gave compound 17 as a yellow oil (5.23g, quant.)
Reference: [1] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 1563 - 1569
[2] Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 9, p. 603 - 611
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6736 - 6739
[4] Patent: WO2005/84653, 2005, A2, . Location in patent: Page/Page column 42
[5] British Journal of Pharmacology, 2017, vol. 174, # 14, p. 2287 - 2301
[6] Patent: WO2005/84653, 2005, A2, . Location in patent: Page/Page column 42
  • 4
  • [ 3181-38-2 ]
  • [ 5987-73-5 ]
YieldReaction ConditionsOperation in experiment
96% With thionyl chloride; N,N-dimethyl-formamide In chloroform To a solution of triacetoxy inosine (3. 00g, 7. 63mol) in CHC13 (25mL) was added DMF (1. 80mL, 22.9mmol) and thionyl chloride (1. 68mL, 22. 9mmol) and the resulting solution was refluxed overnight before removal of the solvents in vacuo. The residue was then partitioned between DCM and aq. NaHCO3 and the separated organic phase was washed with brine and dried over MgS04 to afford triacetoxy 6-chloroadenosine as apale yellow oil (3.03g, 96percent).
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 11, p. 2937 - 2942
[2] Tetrahedron Letters, 2000, vol. 41, # 11, p. 1695 - 1697
[3] Organic and Biomolecular Chemistry, 2005, vol. 3, # 3, p. 462 - 470
[4] Patent: WO2005/54269, 2005, A1, . Location in patent: Page/Page column 14
[5] Monatshefte fur Chemie, 2003, vol. 134, # 6, p. 851 - 873
[6] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 6, p. 695 - 698
[7] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 782 - 793
[8] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 7, p. 534 - 537
[9] Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2664 - 2667
[10] Journal of Medicinal Chemistry, 1985, vol. 28, # 11, p. 1636 - 1643
[11] Journal of Labelled Compounds and Radiopharmaceuticals, 2000, vol. 43, # 1, p. 11 - 28
[12] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 5, p. 859 - 866
[13] Patent: EP2407474, 2012, A1, . Location in patent: Page/Page column 5
[14] Journal of Medicinal Chemistry, 2012, vol. 55, # 18, p. 8066 - 8074,9
[15] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6248 - 6263
  • 5
  • [ 87-42-3 ]
  • [ 13035-61-5 ]
  • [ 5987-73-5 ]
YieldReaction ConditionsOperation in experiment
69% With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 60℃; Molecular sieve; Inert atmosphere 10145] Compound LCDO6 was synthesized under standard glycosylation conditions. Briefly, 3-D-ribofuranose 1,2,3,5- tetraacetate (5.5 g, 17.3 mmol) and 6-chloropurine (2.7 g, 17.3 mmol) were dissolved in anhydrous MeCN (50 mL) containing molecular sieves (MS 4 A), followed by the addition ofTMSOTf (300 pL) at 0°C. under argon protection. The reaction mixture was heated at 60°C. overnight and quenched by addition of triethylamine to pH 7. The solvents were then removed and column chromatography (methanol :dichloromethane, 1:20) gave the product as a yellowish solid (4.9 g, 69percent). ‘H NMR (400 MHz, CDC13) ö 8.77 (s, 1H, H-8), 8.24 (s, 1H, H-2), 6.23 (d, 1H, J=5.4 Hz, H-i’), 5.94 (dd, 1H, J=5.4, 5.0 Hz, H-2’), 5.63 (dd, 1H, J=5.0, 4.5 Hz, H-3’), 4.35 (m, 3H, H-4’, H-5’), 2.26 (s, 3H, CH3), 2.07 (s, 3H, CH3), 2.01 (s, 3H, CH3).
Reference: [1] Chinese Chemical Letters, 2011, vol. 22, # 12, p. 1439 - 1442
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3058 - 3065
[3] Patent: US2016/185805, 2016, A1, . Location in patent: Paragraph 0144; 0145
[4] Nucleosides, nucleotides and nucleic acids, 2002, vol. 21, # 1, p. 73 - 78
  • 6
  • [ 7387-57-7 ]
  • [ 5987-73-5 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 74, # 1-4, p. 249 - 260
[2] Journal of Organic Chemistry, 1980, vol. 45, # 20, p. 3969 - 3974
[3] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 666 - 669
[4] Journal of Organic Chemistry, 2002, vol. 67, # 19, p. 6788 - 6796
  • 7
  • [ 108-24-7 ]
  • [ 58-63-9 ]
  • [ 5987-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 18, p. 8066 - 8074,9
  • 8
  • [ 16321-99-6 ]
  • [ 5987-73-5 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 19, p. 6788 - 6796
[2] Synthesis, 1982, # 8, p. 670 - 672
  • 9
  • [ 16321-99-6 ]
  • [ 5987-73-5 ]
  • [ 5987-76-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 241 - 252
  • 10
  • [ 108-24-7 ]
  • [ 2004-06-0 ]
  • [ 5987-73-5 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14702 - 14706
[2] Organic Letters, 2015, vol. 17, # 6, p. 1513 - 1516
  • 11
  • [ 87-42-3 ]
  • [ 13035-61-5 ]
  • [ 5987-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 4, p. 1478 - 1489
  • 12
  • [ 58-63-9 ]
  • [ 5987-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 782 - 793
[2] Organic and Biomolecular Chemistry, 2005, vol. 3, # 3, p. 462 - 470
[3] Monatshefte fur Chemie, 2003, vol. 134, # 6, p. 851 - 873
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2000, vol. 43, # 1, p. 11 - 28
[5] Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2664 - 2667
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 11, p. 2937 - 2942
[7] Patent: EP2407474, 2012, A1,
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6248 - 6263
  • 13
  • [ 79-37-8 ]
  • [ 3181-38-2 ]
  • [ 5987-73-5 ]
Reference: [1] Patent: US4992535, 1991, A,
  • 14
  • [ 32865-86-4 ]
  • [ 13035-61-5 ]
  • [ 5987-73-5 ]
Reference: [1] Chemische Berichte, 1980, vol. 113, # 9, p. 2891 - 2915
  • 15
  • [ 87-42-3 ]
  • [ 13035-61-5 ]
  • [ 5987-73-5 ]
  • [ 515866-05-4 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 23, p. 6369 - 6381
  • 16
  • [ 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
  • 17
  • [ 58-63-9 ]
  • [ 5987-73-5 ]
Reference: [1] British Journal of Pharmacology, 2017, vol. 174, # 14, p. 2287 - 2301
[2] Patent: WO2005/84653, 2005, A2,
  • 18
  • [ 87-42-3 ]
  • [ 5987-73-5 ]
Reference: [1] Chemische Berichte, 1980, vol. 113, # 9, p. 2891 - 2915
  • 19
  • [ 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
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