2′-O-Methyladenosine CAS#: 2140-79-6; 凯望编码 (ChemWhat Code): 96875
Identification
| 英文名 | 2′-O-Methyladenosine |
| IUPAC Name | (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol |
| 分子结构 |  |
| CAS编号 | 2140-79-6 |
| MDL Number | MFCD00056002 |
| 别名 | 2′-O-Methyladenosine 2140-79-6 Adenosine, 2′-O-methyl- (2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxytetrahydrofuran-3-ol 2′-O-Methyl adenosine (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol CHEMBL73237 2′-O-METHYL-ADENOSINE 02YX82IHZ5 CHEBI:69426 cordysinin B MFCD00056002 C11H15N5O4 UNII-02YX82IHZ5 SCHEMBL25936 2′-O-Me-A DTXSID50175671 BCP17411 BDBM50144945 HG1274 PDSP1_001054 PDSP2_001038 AKOS016003815 AC-8216 CS-W012268 HY-W011552 (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxy-tetrahydrofuran-3-ol BP-58835 DS-14586 PD018166 Q63392855 5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol |
| 分子式 | C11H15N5O4 |
| 分子量 | 281.27 |
| InChI | InChI=1S/C11H15N5O4/c1-19-8-7(18)5(2-17)20-11(8)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1 |
| InChI Key | FPUGCISOLXNPPC-IOSLPCCCSA-N |
| Isomeric SMILES | CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)CO)O |
Physical Data
| Appearance | White powder |
| Melting Point, °C | Solvent (Melting Point) |
| 204 – 206 | |
| 202 – 203 | ethanol |
| 200 – 201 | |
| 198 – 201 | |
| 203 – 207 |
| Density, g·cm-3 |
| 1.482 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | 25 | ||
| Chemical shifts | 1H | dimethylsulfoxide-d6 | 25 | 500 |
| Chemical shifts | 13C | dimethylsulfoxide-d6 | 125 | |
| Chemical shifts | 1H | CD3OD | 500 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Comment (IR Spectroscopy) |
| Bands | neat (no solvent, solid phase) | |
| Bands | potassium bromide |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Comment (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm | Ext./Abs. Coefficient, l·mol-1cm-1 |
| Absorption maxima | H2O | 259 | 14000 | |
| Absorption maxima | 259 | 400 | ||
| Absorption maxima | H2O | Remark: pH 7 | 259 | 13804 |
Route of Synthesis (ROS)
| Conditions | Yield |
| With 1H-imidazole In pyridine at 65℃; for 12h; silylation; | 93% |
| With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 28h; | 83% |
| With pyridine; 1H-imidazole at 20℃; for 15h; Experimental Procedure 117-130 Preparation of compound 7-2: To a solution of 7-1 (15.0 g, 53.3 mmol) in dry pyridine (150 mL) was added TBSC1 (20.0 g, 133.3 mmol) and Imidazole (10.8 g, 159.9 mmol). The mixture was stirred at r.t. for l5h. TLC showed 7-1 was consumed completely. The reaction mixture was concentrated in vacuo to give residue. The residue was quenched with DCM (500 mL). The DCM layer was washed with H2O (1 L*2) 2 times and brine. The DCM layer concentrated in vacuo to give crude 7-2 (27.2 g, 53.3 mmol) as a yellow oil. The crude 7-2 was used in next step directly. ESI-LCMS m/z 510.5 [M+H]+. | 99% |
Safety and Hazards
No data available
Other Data
No data available
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 281.271 |
| logP | -1.327 |
| HBA | 9 |
| HBD | 3 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 128.54 |
| Rotatable Bond (RotB) | 3 |
| Matching Veber Rules | 2 |
| Quantitative Results | ||
| 1 of 25 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | Novel adenosine derivatives and pharmaceutical composition containing them as an active ingredient | |
| 2 of 25 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | Methylation of Adenosine and Related Nucleosides with Trimethylselenonium Hydroxyde, and Regiospecific Effects of Copper(II) Ions | |
| 3 of 25 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | Nucleic acid related compounds. 36. Synthesis of the 2′-O-methyl and 3′-O-methyl ethers of guanosine and 2-aminoguanosine and correlation of O’-methylnucleoside 13C nmr spectral shifts | |
| 4 of 25 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | The first synthesis of herbicidin B. stereoselective construction of the tricyclic undecose moiety by a conformational restriction strategy using steric repulsion between adjacent bulky silyl protecting groups on a pyranose ring | |
| 5 of 25 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | Inhibitory actvity of the compound against Fatty acid amide hydrolase in 0.1 M sodium phosphate, pH 8.0 | |
| 6 of 25 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | Recognition and detection of 8-oxo-rG in RNA using the DNA/OMeRNA chimera probes containing fluorescent adenosine-diazaphenoxazine analog | |
| 7 of 25 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase | |
| 8 of 25 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | RNAi agents and compositions for inhibiting expression of apolipoprotein C-III (APOC3) | |
| 9 of 25 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | MODIFIED SHORT INTERFERING NUCLEIC ACID (SINA) MOLECULES AND USES THEREOF | |
| 10 of 25 | Comment (Pharmacological Data) | Bioactivities present |
| Reference | Adolescent alcohol exposure changes RNA modifications in adult brain by mass spectrometry-based comprehensive profiling analysis |
| Use Pattern |
| 2′-O-Methyladenosine CAS#: 2140-79-6 （N-EPSILON-L-LYSINE METHYL ESTER HYDROCHLORIDE SALT and it is used in IVD. |
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