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CAS No. : | 38819-10-2 | MDL No. : | MFCD00065486 |
Formula : | C10H13N5O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NYHBQMYGNKIUIF-FJFJXFQQSA-N |
M.W : | 283.24 | Pubchem ID : | 135499520 |
Synonyms : |
AraG;ara-Guanosine;Ara-G , ara-Guanosine, Guanine Arabinoside;NSC 76352;Guanine Arabinoside
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 5.0 |
Molar Refractivity : | 65.5 |
TPSA : | 159.51 Ų |
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) : | -9.37 cm/s |
Log Po/w (iLOGP) : | 0.64 |
Log Po/w (XLOGP3) : | -1.89 |
Log Po/w (WLOGP) : | -3.0 |
Log Po/w (MLOGP) : | -1.95 |
Log Po/w (SILICOS-IT) : | -2.22 |
Consensus Log Po/w : | -1.68 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.61 |
Solubility : | 70.1 mg/ml ; 0.248 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.94 |
Solubility : | 32.5 mg/ml ; 0.115 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.51 |
Solubility : | 910.0 mg/ml ; 3.21 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.86 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 12h;Inert atmosphere; | [0230] To a solution of PH- 13 (50 g, 95.10mmol, 1.00equiv) in tetrahydrofuran (500 mL) with an inert atmosphere of nitrogen, was added tetrabutylammonium fluoride (95 mL, 1.00equiv, 1N in tetrahydrofuran). The resulting mixture was stirred for 12 h at 20oC. The resulting mixture was concentrated under reduced pressure. The crude was re-crystallized from methanol/ethyl acetate in the ratio of 1/5 (20 ml/g) three times. The solids were collected by filtration, and then purified by Flash with the following conditions: Column, C18 silica gel; mobile phase, waters and acetonitrile (2% acetonitrile up to 10% in 10 min); Detector, UV 254 nm. This resulted in 16 g (59%) of PH- 14 as a brown solid.1H-NMR (DMSO-d6, 400MHz): 10.44(s, 1H), 6.49(s, 2H), 6.02(s, 1H), 5.55-5.65(m, 2H), 5.10(s, 1H), 4.08(m, 2H), 3.76(m, 1H), 3.64(m, 1H). |
59% | With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 12h;Inert atmosphere; | To a solution of PH- 13 (50 g, 95.l0mmol, l .OOequiv) in tetrahydrofuran (500 mL) with an inert atmosphere of nitrogen, was added tetrabutylammonium fluoride (95 mL, l .OOequiv, 1N in tetrahydrofuran). The resulting mixture was stirred for 12 h at 20C. The resulting mixture was concentrated under reduced pressure. The crude was re-crystallized from methanol/ethyl acetate in the ratio of 1/5 (20 ml/g) three times. The solids were collected by filtration, and then purified by Plash with the following conditions: Column, Cl 8 silica gel; mobile phase, waters and acetonitrile (2% acetonitrile up to 10% in 10 min); Detector, UV 254 nm. This resulted in 16 g (59%) of PH- 14 as a brown solid. 1H-NMR (DMSO-i/e, 400MHz): l0.44(s, 1H), 6.49(s, 2H), 6.02(s, 1H), 5.55- 5.65(m, 2H), 5T0(s, 1H), 4.08(m, 2H), 3.76(m, 1H), 3.64(m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.8% | With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20℃; for 18h; | To a stirred solution of compound 15-1 (5.0 g, 17.7 mmol) in dry DMF (30 mL) were added imidazole (2.4 mL, 35.4 mmol) and TBSCl (5.3 g, 35.4 mmol) at 0° C. The mixture was then stirred at R.T. for 18 hour. The reaction mixture was cooled to 0° C. and quenched with ice water. The resulting precipitate was collected and washed with water and acetone to give compound 15-2 (6.3 g, yield 89.8percent) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 10.58 (s, 1H), 7.69 (s, 1H), 6.46 (s, 2H), 5.99 (d, J=4.4 Hz, 1H), 5.62 (d, J=4.8 Hz, 1H), 5.52 (d, J=4.4 Hz, 1H), 4.04-4.09 (m, 2H), 3.71-3.85 (m, 2H), 0.88 (s, 9H), 0.04 (s, 6H); ESI-MS: m/z=398 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | [0231] To solution of PH-14 (220 g, 776.72mmol, 1.00equiv) in N,N-dimethylformamide (2000 mL) with an inert atmosphere of argon, was added triphenylphosphine (509 g, 1.94mol, 2.50equiv). The resulting solution was stirred for 1.5 h at 0oC. To this was added diethyl azodicarboxylate (338 g, 1.94mol, 2.50equiv) dropwise with stirring at 0oC. The resulting solution was stirred for 2 h at room temperature. The resulting mixture was poured into 20 L cold ethyl ether. The solids were collected by filtration, then re-crystallized from methanol/ ethyl acetate in the ratio of 1/10 (10 ml/g). This resulted in 100 g (49%) of PH-15 as a brown solid. MS m/z [M+H]+ (ESI): 266. | |
49% | To solution of PH-14 (220 g, 776.72mmol, 1.OOequiv) in N,N-dimethylformamide (2000 mL) with an inert atmosphere of argon, was added triphenylphosphine (509 g, l .94mol, 2.50equiv). The resulting solution was stirred for 1.5 h at 0C. To this was added diethyl azodicarboxylate (338 g, l .94mol, 2.50equiv) dropwise with stirring at 0C. The resulting solution was stirred for 2 h at room temperature. The resulting mixture was poured into 20 L cold ethyl ether. The solids were collected by filtration, then re-crystallized from methanol/ ethyl acetate in the ratio of 1/10 (10 ml/g). This resulted in 100 g (49%) of PH-15 as a brown solid. MS m/z [M+H]+ (ESI): 266. |