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[ CAS No. 6979-94-8 ] {[proInfo.proName]}

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Chemical Structure| 6979-94-8
Chemical Structure| 6979-94-8
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Product Details of [ 6979-94-8 ]

CAS No. :6979-94-8 MDL No. :MFCD00057054
Formula : C16H19N5O8 Boiling Point : -
Linear Structure Formula :- InChI Key :ULXDFYDZZFYGIY-SDBHATRESA-N
M.W : 409.35 Pubchem ID :135465084
Synonyms :
2',3',5'-Triacetylguanosine

Calculated chemistry of [ 6979-94-8 ]

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 : 2.0
Molar Refractivity : 94.71
TPSA : 177.72 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) : -9.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : -0.72
Log Po/w (WLOGP) : -1.29
Log Po/w (MLOGP) : -1.21
Log Po/w (SILICOS-IT) : -0.91
Consensus Log Po/w : -0.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.63
Solubility : 9.68 mg/ml ; 0.0237 mol/l
Class : Very soluble
Log S (Ali) : -2.54
Solubility : 1.19 mg/ml ; 0.00291 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.36
Solubility : 17.7 mg/ml ; 0.0432 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.48

Safety of [ 6979-94-8 ]

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 [ 6979-94-8 ]

* 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 [ 6979-94-8 ]
  • Downstream synthetic route of [ 6979-94-8 ]

[ 6979-94-8 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 6979-94-8 ]
  • [ 1818-71-9 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 3, p. 406 - 408
  • 2
  • [ 6979-94-8 ]
  • [ 2140-67-2 ]
Reference: [1] Canadian Journal of Chemistry, 2001, vol. 79, # 12, p. 1881 - 1886
  • 3
  • [ 108-24-7 ]
  • [ 118-00-3 ]
  • [ 6979-94-8 ]
YieldReaction ConditionsOperation in experiment
98% With dmap; triethylamine In acetonitrile at 0 - 20℃; for 3 h; 2.2 mL of acetic anhydride (22 mmol) was added dropwise to a suspension of guanosine (2 g, 7.0 mmol) (dried for 2 days over P4O10 in high vacuum), triethylamine (7.7 mL, 55.2 mmol) and N,N-(dimethylamino)pyridine (92 mg, 0.75 mmol) in 27 mL of acetonitrile at 0 °C. The mixture was stirred until it became homogeneous and kept an additional 3 h at room temperature. The reaction was quenched with methanol (2.3 mL). The volume was reduced to 1/3 using a rotary evaporator and diethyl ether was added dropwise to induce precipitation of a fine white powder. The product was collected by filtration, washed with diethyl ether, and then stirred for 2 hr with acetone (30 mL) at 50 °C. The filtrate produced 2.8 g (98percent) of a fine white powder. 1H NMR (200 MHz, DMSO) δ 10.54 (s, 1H, NH) 7.93 (s, 1H, H-8), 6.34 (br, 2H, NH2), 5.98 (d, J = 6.1 Hz, 1H, H-1'), 5.79 (t, J = 5.8 Hz, 1H, H-2'), 5.51-5.48 (m, 1H, H-3'), 4.40-4.37 (m, 1H, H-4'), 4.33-4.31 (m, 1H, H-5'), 4.23-4.28 (m, 1H, H-5), 2.11 (s, 3H, CH3, acetyl), 2.05 (s, 3H, CH3, acetyl), 2.04 (s, 3H, CH3, acetyl); 13C NMR (200 MHz, CDCl3) δ 172.1 (CO), 171.0 (CO), 169.9 (CO), 156.3 (C-6), 152.8 (C-2), 151.2 (C-4), 137.6 (C-8), 119.6 (C-5), 86.1 (C-1'), 82.3 (C-4'), 73.6 (C-2'), 72.3 (C-3'), 61.8 (C-5'), 21.1 (C, acetyl), 20.6 (C, acetyl), 20.2 (C, acetyl); m/z: calcd for C18H21N5O5 (M+H)+: 410.1306, found: 410.1305.
98% With dmap; triethylamine In acetonitrile at 0 - 20℃; for 1 h; 2.2 mL of acetic anhydride (22 mmol) was added dropwise to a suspension of commercially available guanosine (2 g, 7.0 mmol), triethylamine (7.7 mL, 55.2 mmol) and N,N-(dimethylamino)pyridine (92 mg, 0.75 mmol) in 27 mL of acetonitrile at 0oC. The mixture was stirred until it became homogeneous and kept an additional 1 hr at room temperature. The reaction was quenched with methanol (2.3 mL). The volume was reduced to 1/3 using a rotary evaporator and diethyl ether was added dropwise to induce precipitation of a fine white powder. The product was collected by filtration, washed with diethyl ether, and then stirred for 2 hr with acetone (30 mL) at 50 C. The filtrate produced 2.8 g (98percent) of a fine white powder.
96% With pyridine In DMF (N,N-dimethyl-formamide) at 75 - 80℃; for 3.75 h; A suspension of 113 g (0.4 mol) of dry guanosine (6.1), acetic anhydride (240 mL, 2.5 mol), dry pyridine (120 mL) and dry DMF (320 mL) was heated for 3.75 hours at 75°C without allowing the temperature to exceed 80°C. The clear solution was then transferred to a 3L Erlenmyer flask and filled with 2-propanol. Upon cooling the solution to room temperature crystallization was initiated and allowed to proceed at 4°C overnight. The white solid filtrate was filtered, washed with 2-propanol and recrystallized from 2-propanol to give 6.2 (96percent). 1H NMR (300 Mhz, CDCl3) δ 8.20 (s, 1H, H-8), 6.17 (d, J= 5.41 Hz, 1 H, H-1') 5.75 (t, J= 5.39 Hz, 1H, H-2'), 5.56 (t, J = 5.0, H-3'), 4.41 (m, 3H, H-4',5'), 2.14 (s, 3H, Ac), 2.11 (s, 3H, Ac), 2.10 (s, 3H, Ac). 13C NMR (300 MHz, CD3OD) δ 171.0, 170.3, 1702, 157.7, 154.8, 152.4, 136.7, 117.7, 85.5, 80.4, 73.0, 71.3, 64.0, 31.3, 21.2, 21.0.
96% With dmap; triethylamine In acetonitrile at 20℃; for 0.5 h; Guanosine 1 (11.3 g, 40 mmol) and N,N-dimethylaminopyridine (366 mg, 3 mmol, 0.07 equiv) were dissolved in 500 mL acetonitrile. After addition of triethylamine (22.9 mL, 158.4 mmol) and Ac2O (13.6 mL, 144 mmol), the mixture was stirred at room temperature for 30 min. The reaction was quenched by addition of 5 mL MeOH and the solvent evaporated in vacuo. The oily residue was recrystallized from 2-propanol to afford 2 as a white powder (15.7 g, 96percent). mp 229-231 oC (lit.[1] mp 228-229 oC); 1H NMR (300 MHz, DMSO-d6): δ 10.75 (1H, br s, OH), 7.94 (1H, s, H-8), 6.55 (2H, br s, NH2), 5.98 (1H, d, J = 6.2 Hz, H-1'), 5.79 (1H, dd, J = 6.0, 6.2 Hz, H-2'), 5.59 (1H, dd, J = 3.9, 6.0 Hz, H-3'), 4.37 (1H, ddd, J = 3.9, 4.9, 5.5 Hz, H-4'), 4.31(1H, dd, J = 4.9, 12.4 Hz, H-5'a), 4.23 (1H, dd, J = 5.5, 12.4 Hz, H-5'b), 2.11 (3H, s, CH3CO), 2.04 (3H, s, CH3CO), 2.03 (3H, s, CH3CO).
80% With dmap; triethylamine In acetonitrile at 20℃; for 2 h; Cooling with ice To a stirred suspension of guanosine (5.0 g, 17.7 mmol) in MeCN (65 mL) was added Et3N (6.47 mL, 46.5 mmol) and DMAP (0.22 g, 1.8mmol). The resulting suspension was cooled in an ice bath prior to dropwise addition of Ac2O (5.84 mL, 61.84 mmol). Once the addition was completed, the mixture was allowed to reach room temperature and was stirred for a further 2 h. The reaction was quenched by the addition of MeOH (6.5 mL) and concentrated in vacuo to a white semi-solid precipitate which was boiled with iPrOH and filtered, leaving the product as a white solid. (5.79 g, 80percent). 1H NMR (500 MHz, DMSO-d6): δ (ppm) 10.70 (1H, s, NH); 7.91 (1H, s, H8); 6.49 (2H, s, NH2); 5.98 (1H, d, 3JH1'H2' = 6.1Hz, H1'); 5.79 (1H, t, 3JH2'H3' = 6.0 Hz, H2'); 5.50 (1H, dd, 3JH3'H4' = 4.2, H3'); 4.37 (1H, dd, 3JH5''H4' = 3.8 and 2JH5H5 =11.5 Hz, H5); 4.31 (1H, m, H4); 4.26 (1H, dd, 3JH5H4 = 5.7 Hz, H5'); 2.11 [3H, s, (CH3)3']; 2.04 [3H, s, (CH3)5']; 2.03 [3H, s, (CH3)2']. 13C NMR (125 MHz, DMSOd6): δ (ppm) 170.89 [(CO)5']; 170.24 [(CO)3']; 170.07 [(CO)2']; 157.46 (C6); 154.75 (C2); 151.95 (C4); 136.45 (C8); 117.74 (C5); 85.35 (C1'); 80.40 (C4'); 72.93 (C2'); 71.18 (C3'); 63.92 (C5'); 21.34 [(CH3)5']; 21.20 [(CH3)3'] and 21.01 [(CH3)2'].
79% With dmap; N,N-dimethyl-ethanamine In acetonitrile at 20℃; for 1 h; Guanosine (6) 8.40 g (29.7 mmol) and 0.2 g of dimethylaminopyridine were suspended in a mixture of ethyldimethylamine 8.8 g (120 mmol), acetic anhydride 10.2 g (100 mmol) and acetonitrile 100 mL. The reaction mixture was stirred for 60 minutes at room temperature until the solution becomes clear. Methanol was added to the reaction mixture and the solvents were removed under vacuum. The product was recrystallized from isopropanol, washed with acetone and dried to give 6a as pure product. Yield 9.6 g (79percent)
75% With pyridine In N,N-dimethyl-formamide at 60 - 100℃; for 4 h; Step A:
Preparation of 2',3',5'-Tri-O-acetylguanosine
A 12-liter, 3-necked, round bottom flask equipped with a mechanical stirrer, dropping funnel, condenser, and argon inlet is charged with dimethylformamide (9 liters) and guanosine (predried for 20 hours at 80° C. over P4O10, 988 g, 3.50 moles), then heated to 60° C. Pyridine (1.1 liters) followed by acetic anhydride (2.15 liters, 22.8 moles) is added and the mixture heated to 90-100° C. for 4 hours.
After cooling to room temperature overnight, the mixture is evaporated to remove approximately 6 liters, then slurried with 10 liters of isopropanol while heating to 70° C. for 1 hour.
The mixture is slowly cooled to room temperature, affording the product as a crystalline solid.
After collecting by filtration, the solid is washed with isopropanol (2*2 liters), then dried under vacuum at 80° C. for 17 hours to provide the desired intermediate (1,080 g, 75percent).
70% With pyridine In N,N-dimethyl-formamide at 75℃; for 4.15 h; Guanosine (1) (90 g, 387.9 mmol) was dissolved in dry pyridine and DMF (95.4 mL) followed by the addition of acetic anhydride (191.15 mL, 2420.0 mmol) and the reaction mixture was stirred at 75 °C for 4.15 h. The resultant clear solution was mixed with 2-propanol and maintained at 4 °C for overnight to afford white solid which was recrystallized from 2-propanol,10percent methanol in chloroform to afforded compound2in 70percent yield.Spectral data is consistent with the literature.

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  • 4
  • [ 2466-76-4 ]
  • [ 118-00-3 ]
  • [ 6979-94-8 ]
YieldReaction ConditionsOperation in experiment
53% With sodium hydroxide In water at 20℃; for 4 h; General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.
Reference: [1] Synlett, 2017, vol. 28, # 1, p. 78 - 83
  • 5
  • [ 335060-31-6 ]
  • [ 6979-94-8 ]
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  • 6
  • [ 92123-04-1 ]
  • [ 6979-94-8 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, p. 2048 - 2051
  • 7
  • [ 335060-20-3 ]
  • [ 6979-94-8 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2001, vol. 20, # 1-2, p. 59 - 75
  • 8
  • [ 335060-33-8 ]
  • [ 6979-94-8 ]
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  • 9
  • [ 94042-04-3 ]
  • [ 52921-40-1 ]
  • [ 1579969-28-0 ]
  • [ 6979-94-8 ]
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  • 10
  • [ 172224-98-5 ]
  • [ 6979-94-8 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 43, p. 7881 - 7884
  • 11
  • [ 6979-94-8 ]
  • [ 2004-07-1 ]
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[2] ChemMedChem, 2011, vol. 6, # 6, p. 1074 - 1080
[3] Carbohydrate Research, 2017, vol. 452, p. 91 - 96
  • 12
  • [ 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
  • 13
  • [ 6979-94-8 ]
  • [ 35109-88-7 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 20, p. 6747 - 6754
[2] Journal of Organic Chemistry, 1985, vol. 50, # 3, p. 406 - 408
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 34, p. 8913 - 8918[4] Angew. Chem., 2014, vol. 126, # 34, p. 9059 - 9064,6
[5] Organic and Biomolecular Chemistry, 2015, vol. 13, # 31, p. 8550 - 8555
[6] Journal of Medicinal Chemistry, 2016, vol. 59, # 22, p. 10322 - 10328
[7] Tetrahedron Letters, 2017, vol. 58, # 44, p. 4166 - 4168
[8] ChemBioChem, 2017, vol. 18, # 21, p. 2156 - 2164
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