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CAS No.: | 1463-10-1 |
---|---|
Name: | 5-Methyluridine |
Article Data: | 71 |
Molecular Structure: | |
Formula: | C10H14N2O6 |
Molecular Weight: | 258.231 |
Synonyms: | 1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione;Uridine,5-methyl-;5-Methyl uridine;Thymine riboside;Methyluridine;5-Methyluridin, Ribothymidine; |
EINECS: | 215-973-9 |
Density: | 1.576 g/cm3 |
Melting Point: | 183-184 °C(lit.) |
Appearance: | white powder |
Hazard Symbols: | T+ |
Risk Codes: | 26/27/28 |
Safety: | 24/25 |
PSA: | 124.78000 |
LogP: | -2.54350 |
Conditions | Yield |
---|---|
With sodium methylate In methanol | 98% |
With ammonia In methanol for 96h; | 98% |
With sodium methylate In methanol for 0.5h; Heating; | 93% |
2',3',5'-tri-O-benzoyluridine
A
benzoic acid ethyl ester
B
benzamide
C
5-Methyluridine
Conditions | Yield |
---|---|
With ammonia In ethanol at 20℃; | A n/a B n/a C 95% |
1-(5'-O-trityl-β-D-ribofuranosyl)thymine
5-Methyluridine
Conditions | Yield |
---|---|
With carbon tetrabromide In methanol at 20℃; for 12h; Irradiation; | 94% |
With sulfuric acid; water; silica gel In acetonitrile at 25℃; for 0.283333h; | 93% |
1-[5'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine
5-Methyluridine
Conditions | Yield |
---|---|
With chloro-methylsulfanyl-methane; water; potassium iodide In 1,4-dioxane at 50℃; for 5.3h; | 93% |
Conditions | Yield |
---|---|
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Irradiation; chemoselective reaction; | 88% |
2',3'-O-isopropylidene-5'-O-methoxymethyl-5-methyluridine
5-Methyluridine
Conditions | Yield |
---|---|
With trifluoroacetic acid for 19h; Ambient temperature; | 87% |
1,2,3,5-tetra-O-acetyl-β-L-ribofuranose
2,4-bis(trimethylsiloxy)-5-methylpyrimidine
5-Methyluridine
Conditions | Yield |
---|---|
Stage #1: 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose; 2,4-bis(trimethylsiloxy)-5-methylpyrimidine With tin(IV) chloride In dichloromethane for 12h; Reflux; Stage #2: With acetic acid In dichloromethane at 20℃; for 1h; Stage #3: With ammonia In methanol at 20℃; for 12h; | 85.06% |
Conditions | Yield |
---|---|
With purine nucleoside phosphorylase; uridine phosphorylase at 90℃; for 48h; pH=9; aq. phosphate buffer; Enzymatic reaction; | 85% |
In water; dimethyl sulfoxide at 25℃; pH=7.4; aq. phosphate buffer; Enzymatic reaction; | 79.1% |
(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
5-Methyluridine
Conditions | Yield |
---|---|
With ammonia In methanol at 20℃; for 6h; Inert atmosphere; Schlenk technique; | 81% |
With ammonia In methanol at 20℃; | |
With Amberlite IRA 120 H+ In 1,4-dioxane; methanol | 14.1 g |
5-(2,5-dimethoxythiophenyl)-5-methyl-5,6-dihydrouridine
5-Methyluridine
Conditions | Yield |
---|---|
In water for 0.0666667h; Photolysis; | 78% |
Molecule structure of 5-Methyluridine (CAS NO.1463-10-1):
IUPAC Name: 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
Molecular Weight: 258.22796 g/mol
Molecular Formula: C10H14N2O6
Density: 1.576 g/cm3
Melting Point: 183-184 °C(lit.)
Index of Refraction: 1.618
Molar Refractivity: 57.43 cm3
Molar Volume: 163.7 cm3
Surface Tension: 75.9 dyne/cm
Storage Temp.: 2-8 °C
XLogP3: -1.6
H-Bond Donor: 4
H-Bond Acceptor: 6
Rotatable Bond Count: 2
Tautomer Count: 3
Exact Mass: 258.085186
MonoIsotopic Mass: 258.085186
Topological Polar Surface Area: 119
Heavy Atom Count: 18
Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
InChI: InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1
InChIKey: DWRXFEITVBNRMK-JXOAFFINSA-N
EINECS: 215-973-9
Product Categories: Pyridines, Pyrimidines, Purines and Pteredines; Miscellaneous Biochemicals; Nucleotides and Nucleosides; Biochemistry; Nucleosides and their analogs; Nucleosides, Nucleotides & Related Reagents; Bases & Related Reagents; Nucleotides
Hazard Codes: T+
Risk Statements: 26/27/28
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
5-Methyluridine (CAS NO.1463-10-1) is also named as Ribothymidine ; Thymine riboside ; Uridine, 5-methyl- . 5-Methyluridine (CAS NO.1463-10-1) is white powder. The stability of 5-methyluridine under standard temperature and pressure (STP) is very high.