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Chemical Structure| 58-96-8
Chemical Structure| 58-96-8
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Product Details of [ 58-96-8 ]

CAS No. :58-96-8 MDL No. :MFCD00006526
Formula : C9H12N2O6 Boiling Point : -
Linear Structure Formula :- InChI Key :DRTQHJPVMGBUCF-XVFCMESISA-N
M.W : 244.20 Pubchem ID :6029
Synonyms :
β-Uridine;NSC 20256;Uracil-1-β-D-ribofuranoside;1-β-D-Ribofuranosyluracil
Chemical Name :1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Calculated chemistry of [ 58-96-8 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.56
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 4.0
Molar Refractivity : 54.27
TPSA : 124.78 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) : -9.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.44
Log Po/w (XLOGP3) : -1.98
Log Po/w (WLOGP) : -3.18
Log Po/w (MLOGP) : -2.64
Log Po/w (SILICOS-IT) : -1.39
Consensus Log Po/w : -1.75

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.24
Solubility : 142.0 mg/ml ; 0.581 mol/l
Class : Very soluble
Log S (Ali) : -0.12
Solubility : 187.0 mg/ml ; 0.764 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.74
Solubility : 1350.0 mg/ml ; 5.55 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.76

Safety of [ 58-96-8 ]

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 [ 58-96-8 ]

* 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 [ 58-96-8 ]
  • Downstream synthetic route of [ 58-96-8 ]

[ 58-96-8 ] Synthesis Path-Upstream   1~32

  • 1
  • [ 58-96-8 ]
  • [ 316-46-1 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1983, # 10, p. 563 - 564
[2] Tetrahedron, 1990, vol. 46, # 8, p. 3093 - 3100
[3] Journal of Fluorine Chemistry, 1983, vol. 23, p. 487
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2547 - 2554
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2547 - 2554
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2547 - 2554
[7] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2547 - 2554
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2547 - 2554
[9] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2547 - 2554
  • 2
  • [ 58-96-8 ]
  • [ 316-46-1 ]
  • [ 119068-03-0 ]
  • [ 119003-30-4 ]
  • [ 119003-30-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2547 - 2554
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2547 - 2554
  • 3
  • [ 58-96-8 ]
  • [ 316-46-1 ]
  • [ 119068-04-1 ]
  • [ 119003-30-4 ]
  • [ 119003-30-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2547 - 2554
  • 4
  • [ 78948-09-1 ]
  • [ 58-96-8 ]
  • [ 316-46-1 ]
  • [ 119068-03-0 ]
  • [ 119003-30-4 ]
  • [ 119003-30-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2547 - 2554
  • 5
  • [ 58-96-8 ]
  • [ 2880-89-9 ]
Reference: [1] Synthesis, 2009, # 23, p. 3957 - 3962
[2] Journal of Organic Chemistry, 1990, vol. 55, # 16, p. 4928 - 4933
[3] Canadian Journal of Chemistry, 1994, vol. 72, # 9, p. 2005 - 2010
[4] Nucleosides, Nucleotides and Nucleic Acids, 2009, vol. 28, # 9, p. 821 - 834
[5] Journal of Biological Chemistry, 1951, vol. 190, p. 95,96
[6] Chemical Communications, 2012, vol. 48, # 45, p. 5587 - 5589
[7] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 249 - 255
  • 6
  • [ 58-96-8 ]
  • [ 957-75-5 ]
YieldReaction ConditionsOperation in experiment
79% With sodium azide; bromoisocyanuric acid monosodium salt In water; acetonitrile at 20℃; for 0.5 h; General procedure: 2'-O-Methyluridine (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile solution(H2O:CH3CN 1:9, 5 mL) under stirring. NaN3 (0.104 g, 1.6 mmol) was added, followed by addition of SMBI (0.101 g, 0.44 mmol) at r.t. and the mixture was stirred. Progress of the reaction was followedby TLC. On completion of the reaction after 1.5 h, the reaction mixture was filtered, evaporated todryness under reduced pressure and coevaporated with acetonitrile (2 × 2 mL). The crude reactionmixture was purified by column chromatography (4percent–6percent MeOH in DCM, v/v) to afford bromonucleoside 6 (0.117 g, 93percent) in pure form as a white solid
75% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at 25℃; for 0.33 h; Typical procedure for the bromination of unprotected nucleosides: DBH (323 mg, 1.13 mmol) was added to a stirred solution of 1d (500 mg, 2.05 mmol) in DMF (5 mL). The resulting pale-yellow solution was stirred at room temperature for 20 minutes or until TLC showed absence of starting material and formation of less polar product. Volatiles were evaporated and the residue was coevaporated with MeCN. The resulting pale solid was crystallized from hot acetone to give 2d (500 mg, 75percent) as colorless crystals with data as reported.14
22 g With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 80℃; for 4 h; To a solution of uridine 146 (20.0 g, 82mmol) and N BS (21 .7 g, 0.12 mol) in anhydrous dimethylfomamide was added AIBN (0.1 eq) in anhydrous dimethylfomamide, then the solution was stirred at 80 °C for 4 h. Saturated sodium thiosulfate solution (20 mL) was added. After evaporation of the solvent, the residue was precipitation with methanol to give 22.0 g compound 147 as light yellow solid.
22.0 g With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 80℃; for 4 h; Synthesis of Compound 147: To a solution of uridine 146 (20.0 g, 82mmol) and NBS (21 .7 g,0.12 mol) in anhydrous dimethylfomamide was added AIBN (0.1 eq) in anhydrous dimethylfomamide,then the solution was stirred at 80 °C for 4 h. Saturated sodium thiosulfate solution (20 mL) was added. After evaporation of the solvent, the residue was precipitation with methanol to give 22.0 g compound 147 as light yellow solid.
22 g With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 80℃; for 4 h; Synthesis of Compound 1 47: To a solution of uridine 146 (20.0 g, 82mmol) and NBS (21 .7 g, 2 mol) in anhydrous dimethylfomamide was added AIBN (0.1 eq) in anhydrous dimethylfomamide, n the solution was stirred at 80 °C for 4 h. Saturated sodium thiosulfate solution (20 mL) was ded. Afte ompound 1
22 g With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 80℃; for 4 h; Synthesis of Compound 147: To a solution of uridine 146 (20.0 g, 82mmol) and NBS (21.7 g, 0.12 mol) in anhydrous dimethylfomamide was added AIBN (0.1 eq) in anhydrous dimethylfomamide, then the solution was stirred at 80 °C for 4 h. Saturated sodium thiosulfate solution (20 mL) was added. After evaporation of the solvent, the residue was precipitation with methanol to give 22.0 g compound 147 as light yellow solid.

Reference: [1] Canadian Journal of Chemistry, 1994, vol. 72, # 9, p. 2005 - 2010
[2] Synthesis, 2009, # 23, p. 3957 - 3962
[3] Journal of Organic Chemistry, 1990, vol. 55, # 16, p. 4928 - 4933
[4] Organic and Biomolecular Chemistry, 2008, vol. 6, # 16, p. 2884 - 2891
[5] Nucleosides, Nucleotides and Nucleic Acids, 2009, vol. 28, # 9, p. 821 - 834
[6] Molecules, 2013, vol. 18, # 10, p. 12740 - 12750
[7] Tetrahedron Letters, 2012, vol. 53, # 26, p. 3333 - 3336
[8] Chemistry - A European Journal, 2009, vol. 15, # 27, p. 6619 - 6625
[9] Recueil: Journal of the Royal Netherlands Chemical Society, 1981, vol. 100, # 7/8, p. 267 - 271
[10] Patent: WO2014/93924, 2014, A1, . Location in patent: Page/Page column 288; 289
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[13] Patent: WO2015/196128, 2015, A2, . Location in patent: Page/Page column 629
[14] Patent: EP2918275, 2015, A1, . Location in patent: Paragraph 2169; 2170
[15] Patent: EP2918275, 2016, B1, . Location in patent: Paragraph 2169; 2170
  • 7
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  • [ 957-75-5 ]
  • [ 114743-19-0 ]
Reference: [1] Synthesis, 1987, vol. No. 9, p. 829 - 831
  • 8
  • [ 14337-14-5 ]
  • [ 58-96-8 ]
  • [ 957-75-5 ]
Reference: [1] Inorganica Chimica Acta, [2] Inorganica Chimica Acta, 1990, vol. 168, p. 221 - 226
[3] Inorganica Chimica Acta, [4] Inorganica Chimica Acta, 1990, vol. 168, p. 221 - 226
  • 9
  • [ 58-96-8 ]
  • [ 1024-99-3 ]
YieldReaction ConditionsOperation in experiment
92% With iodine; nitric acid In chloroform at 80℃; for 5 h; In a round bottom flask, uridine (1 g, 4.1 mmol) and iodine powder (1 .15 g, 4.5 mmol) were dissolved in a mixture of CHCI3 (55 ml) and 1 M HN03 (10 ml). The reaction was heated at reflux (80°C) for 5h. Reaction progress was monitored by TLC (30 percent methanol in chloroform, Rf: 0.60; RfsM: 0.45). Upon cooling of the reaction mixture to 4°C, crystals of the title compound formed as colourless needles. The precipitate was collected by filtration and dried under vacuum overnight to provide 1.39 g (92 percent) of 5-iodouridine 1 ; δΗ (DMSO-d6, 300 MHz) 3.49 - 3.71 (2H, m, H-5'), 3.84 - 3.88 (1 H, m, H-4'), 3.98 (1 H, t, J = 5.0 Hz, H-3'), 4.02 (1 H, t, J = 5.0 Hz, H-2'), 5.08 (1 H, d, J = 5.3 Hz, OH-3'), 5.27 (1 H, t, J = 4.7 Hz, OH-5'), 5.43 (1 H, d, J = 5.4 Hz, OH- 2'), 5.71 (1 H, d, J = 4.6 Hz, H-1 '), 8.48 (1 H, s, H-6) 1 1 .69 (1 H, s, NH); 5C (DMSO-d6, 300MHz) 61 .2 (C-5'), 70.3 (C-3'), 70.9 (C-5), 75.0 (C-2'), 85.7 (C-4'), 89.5 (C-1 '), 146.0 (C-6), 152.5 (C-2), 162.9 (C-4). m/z (ESI) 388.0000 [M+NH4]+, requires 388.0000.
78% With silver(II) sulfate; iodine In methanol at 20℃; Inert atmosphere Iodine (0.508 g) in 2.0 mL of methanol was added dropwise to a suspension of silver sulfate (0.624 g) and uridine (0.488 g) in 10 mL of methanol. The reaction mixture was stirred at room temperature until the orange color disappeared. The precipitate was removed by filtration. The filtrate was concentrated and recrystallized from methanol, affording a pale yellow solid (78percent). 1HNMR (CD3OD) δ 8.511 (1H, d, J = 3.2 Hz), 5.776 (1H, t, J = 1.6 Hz), 4.085(2H, m), 3.938 (1H, m), 3.814 (1H, d, J = 2.4 Hz), 3.784 (1H, d, J = 2.8 Hz), 3.674 (1H, d, J = 2.4 Hz), 2.644 (1H, d, J = 2.8 Hz); HRMS [M+1] calcd 370.9662, found: 370.9665.
72.2% at 110℃; for 4 h; Take uridine (13.06g, 53.50mmol) was dissolved in 252ml of dilute nitric acid, heated to 110 ,Was added (10.09g, 39.92mmol) elemental iodine, the reaction was monitored by thin layer chromatography case, exhibitionEluent, CH2Cl2: CH3OH = 7: 1, about 4 hours after the reaction raw material point disappears, and the reactionComplete, the reaction was stopped. After leaving to cool and extracted 3 times with 30ml petroleum ether, collecting the lower solution,Upper solution was extracted with 30ml of deionized water, lower solutions were twice extracted. Standing whiteThe solid precipitated, placed in the upper refrigerator overnight, a lot of white solid was obtained, that is, uridine 5-I-(14.30g, 38.64mmol), the yield was 72.22percent
40% With iodine; iodic acid; acetic acid In tetrachloromethane; water at 40℃; for 2 h; General procedure: The suspension of nucleosides 2a,b (19 mmol) in water (5.7 mL) was treated with HIO3(9.7 mmol, 1.7 g), AcOH (15.2 mL) and a solution of iodine (11.22 mmol, 2.85 g) inCCl4 (3.8 mL). The resulting mixture was stirred at 40C for 2 h until the starting materialwas consumed or some by-product was formed (monitored by HPLC). After that,water (20 mL) was added. The reaction mixture was cooled to 4C and filtered. The precipitatewas washed with water (2 £ 10 mL). The combined solutions were diluted withwater (250 ml) and extracted with benzene (3 £ 150 mL). The aqueous layer was evaporatedunder reduced pressure. The product was purified by RPC in a linear gradient ofEtOH in water (0–30percent) to give the product 3a,b.

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[3] Canadian Journal of Chemistry, 1994, vol. 72, # 9, p. 2005 - 2010
[4] Patent: WO2011/51733, 2011, A2, . Location in patent: Page/Page column 44
[5] Synthesis, 2009, # 23, p. 3957 - 3962
[6] Canadian Journal of Chemistry, 1982, vol. 60, p. 554 - 557
[7] Journal of Organic Chemistry, 1990, vol. 55, # 16, p. 4928 - 4933
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[9] Chemical Communications, 2017, vol. 53, # 68, p. 9406 - 9409
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  • 10
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  • 11
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  • [ 606-02-0 ]
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  • 12
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  • 13
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  • 15
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  • 30
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  • [ 103285-22-9 ]
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  • 31
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  • 32
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  • [ 871254-61-4 ]
YieldReaction ConditionsOperation in experiment
96.6%
Stage #1: at 5℃; for 0.5 h;
Stage #2: at 5℃; for 2 h;
In the reaction flask, the solvent DMF (560 mL) was added, the temperature was lowered to 5 ° C, and phosphorus oxychloride (153 g) was slowly added dropwise, and the reaction temperature of the mixed system was controlled not to exceed 5 ° C, and the phosphorus oxychloride was added dropwise. Add boric acid (30.9g), stir for 30min, then add uridine 112g (1mol) in solid form to the above mixed system, control the reaction temperature not to exceed 5 ° C, stir for 2h, slowly warm to room temperature and continue to stir the reaction until The raw materials disappeared. Then, 560 mL of phosphorus oxychloride was added to the reaction system and the temperature was raised to reflux for 6 hours, then phosphorus oxychloride was recovered, and the residue was poured into a rapidly stirred ice water mixture to precipitate 2,4-dichloro-5-pyrimidine formaldehyde solid. 170 g, yield 96.6percent, purity 99.4percent.
Reference: [1] Patent: CN108467368, 2018, A, . Location in patent: Paragraph 0010; 0011; 0012; 0013
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