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| | 2',3'-O-Isopropylideneinosine Basic information |
| Product Name: | 2',3'-O-Isopropylideneinosine | | Synonyms: | 2',3'-isopropylideneinosine;2',3'-O-Isopropylidene-D-inosine;2'',3''-O-ISOPROPYLIDENEINOSINE,98.0+%(LC);2',3'-O-(1-Methylethylidene)- Inosine;9-(2,3-O-Isopropylidene-beta-D-ribofuranosyl)hypoxanthine;2'-O,3'-O-Isopropylidene-2-deaminoguanosine;2'-O,3'-O-Isopropylidene-6-hydroxy-6-deaminoadenosine;2'-O,3'-O-Isopropylideneinosine | | CAS: | 2140-11-6 | | MF: | C13H16N4O5 | | MW: | 308.29 | | EINECS: | 218-388-7 | | Product Categories: | Heterocycles;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Nucleotides | | Mol File: | 2140-11-6.mol |  |
| | 2',3'-O-Isopropylideneinosine Chemical Properties |
| Melting point | 263-272°C | | Boiling point | 606.6±65.0 °C(Predicted) | | density | 1.80±0.1 g/cm3(Predicted) | | storage temp. | Inert atmosphere,2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly, Heated, Sonicated) | | form | Solid | | pka | 14.14±0.10(Predicted) | | color | White to Off-White | | InChI | InChI=1S/C13H16N4O5/c1-13(2)21-8-6(3-18)20-12(9(8)22-13)17-5-16-7-10(17)14-4-15-11(7)19/h4-6,8-9,12,18H,3H2,1-2H3,(H,14,15,19)/t6-,8-,9-,12-/m1/s1 | | InChIKey | LIEKLUBCIPVWQD-WOUKDFQISA-N | | SMILES | OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)O)N=C2)[C@@H]2OC(O[C@H]12)(C)C | | CAS DataBase Reference | 2140-11-6(CAS DataBase Reference) |
| Safety Statements | 24/25 | | WGK Germany | 3 | | HS Code | 29389090 |
| | 2',3'-O-Isopropylideneinosine Usage And Synthesis |
| Chemical Properties | 2',3'-O-Isopropylideneinosine is White Solid | | Uses | A useful precursor for the preparation of nucleic acids | | Uses | 2',3'-O-Isopropylideneinosine is an inosine derivative as antiviral, bactericidal, and antitumor agent for immunopotentiating uses. | | Synthesis | To a solution of inosine (0.998 g, 3.72 mmol) in dimethylformamide (DMF, 30 mL) was sequentially added 2,2-dimethoxypropane (1.8 mL, 14.59 mmol) and p-toluenesulfonic acid monohydrate (0.038 g, 0.372 mmol). The reaction mixture was stirred under argon (Ar) protection for 24 hours. Upon completion of the reaction, DMF was removed by evaporation under reduced pressure, followed by alkalinization of the reaction mixture with 3% ammonia solution and evaporation again to dryness. The resulting residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol, 95/5, v/v) to afford the target compound 22 in white foamy form in 80% yield. The product was characterized by 1H-NMR (200 MHz, DMSO-d6): δ 1.34, 1.50 (6H, s, (CH3)2C), 3.6 (2H, t, CH2-5'), 4.37 (1H, m, H-4'), 4.94 (1H, m, H-3'), 5.18 (1H, t, OH-5'), 5.37 (1H, dd. J = 3.7 Hz, H-2'), 6.12 (1H, d, J = 2.4 Hz, H-1'), 8.05 (1H, s, H-2), 8.32 (1H, s, H-8), and 12.44 (1H, br s, NH-3).ESI-MS analysis showed: m/z 309.1 [M + H]+, molecular formula C13H16N4O5, molecular weight 308.29. | | References | [1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 202 - 209
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 5, p. 2087 - 2103
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 17, p. 5349 - 5370
[4] Heterocycles, 2013, vol. 87, # 11, p. 2369 - 2384
[5] Chinese Chemical Letters, 2011, vol. 22, # 12, p. 1439 - 1442 |
| | 2',3'-O-Isopropylideneinosine Preparation Products And Raw materials |
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