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Chemical Structure| 58-96-8 Chemical Structure| 58-96-8
Chemical Structure| 58-96-8

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Uridin is a nucleoside and one of main component in RNA.

Synonyms: β-Uridine; NSC 20256; Uracil-1-β-D-ribofuranoside

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of Uridine

CAS No. :58-96-8
Formula : C9H12N2O6
M.W : 244.20
SMILES Code : OC[C@@H]1[C@H]([C@H]([C@H](N2C(NC(C=C2)=O)=O)O1)O)O
Synonyms :
β-Uridine; NSC 20256; Uracil-1-β-D-ribofuranoside
English Name :1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
MDL No. :MFCD00006526
InChI Key :DRTQHJPVMGBUCF-XVFCMESISA-N
Pubchem ID :6029

Safety of Uridine

Application In Synthesis of Uridine

* 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.

  • Downstream synthetic route of [ 58-96-8 ]

[ 58-96-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 58-96-8 ]
  • [ 5627-05-4 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen In water for 24h;
96% With hydrogen In methanol for 24h;
With Rh/Al2O3; water Hydrogenation;
With hydrogenchloride; Rh/Al2O3
Multi-step reaction with 2 steps 1: 31 percent / POcl3 / acetonitrile / 1 h / 0 °C 2: 78 percent / H2 / Pd/C / ethanol / 48 h
With Rh/Al2O3; hydrogen In methanol at 21℃; for 6h; Hydrogenation of uridine Uridine (500 mg) was dissolved in 32 ml methanol to which 100 mg Rh/Al2O3were added. This suspension was placed in a Parr Instruments (ParrInstruments, Inc., Moline, IL, USA) stirred reactor using a glass liner. Thereactor was purged with H2 to remove air and charged to 6.6 bar H2 pressure.The reaction was allowed to proceed at 21 °C and gave complete conversion toDHU in 6 h.
With sodium tetrahydroborate; 10% Pd/C; acetic acid In methanol; toluene 3 20mg uridine (Sigma-Aldrich Inc., St. Louis, Mo.) is dissolved in methanol:toluene (1:1 v/v, 2 mL), plus one drop of glacial acetic acid (10 jtL). A catalytic amount of solid palladium on carbon catalyst (10% Pd/C, 3mg) (Sigma Aldrich, St. Louis, Mo.) is added followed by an addition of solid sodium borohydride (7 mg) (Sigma Aldrich, St. Louis, Mo.). The purpose of the acetic acid is to keep the pH mildly acidic (pH 4), so that upon addition of sodium borohydride, the sodium borohydride is degraded to produce hydrogen. The duration for the reaction is determined by a time course experiment, analyzing samples every 2 hours by MALDITOF mass spectrometry. Similarly, the reaction temperature is determined by undertaking the reaction at 20° C., 40° C., 60° C., or 100° C. After these time points, the reaction is cooled to room temperature, and the reaction mixture is filtered through a small cotton pad plus Celite filter (Sigma Aldrich, St. Louis, Mo.) to remove the spent Pd/C catalyst. The filtrate is dried down on an airline, re-dissolved in methanol (2 mL), and heated at 80° C. for 15 minutes. This step results in the conversion of residual sodium borohydride to methyl borate (which is volatile) and residual acetic acid to methyl acetate (also volatile). These volatiles are removed by evaporation on an airline. The residue is dissolved in deuterated water for analysis by NMR using a Bruker AVANCE III instrument (Billerica, MA) to record the spectrum at 500.11 MHz. Control reactions are run that either lacked the Pd/C catalyst (but included the borohydride), or lacked both Pd/C and the sodium borohydride and/or lacked heating.
With Rh/Al2O3; hydrogen In water at 21℃; for 3h; 3.2 Hydrogenation conditions General procedure: The hydrogenations were undertaken as described previously [10]. Briefly, the nucleoside starting material (30mg) in aqueous solution (3mL) were reacted for 3h at room temperature (21 C). Catalyst (5wt% Rh/Al2O3; 20mg) was introduced at the start of the reactions, and hydrogen gas was bubbled through at atmospheric pressure. The products were recovered by filtration to remove the catalyst, followed by lyophilization to remove the water. MALDI/MS spectra were recorded on the aqueous solutions immediately after removal of the catalyst. The lyophilized product residues were re-dissolved in deuterated water for analysis by NMR (1H NMR, 13C NMR, HSQC) without further purification. For the base-catalyzed ring opening reactions, the hydrogenated nucleosides were treated at room temperature for 18h using aqueous sodium hydroxide (0.25M). After neutralization with HCl (0.25M) the samples were analyzed by NMR and MALDI/MS.
94 % In water; formamide UV-irradiation;
In water; formamide UV-irradiation;

  • 2
  • [ 58-96-8 ]
  • [ 2880-89-9 ]
YieldReaction ConditionsOperation in experiment
94% With 1-(2-methoxyethyl)-3-methylimidazolium trifluoroacetate; N-chloro-succinimide at 50℃; for 0.75h;
83% With ammonium cerium(IV) nitrate; lithium chloride In methanol at 80℃;
45% With N-chloro-succinimide; sodium azide In 1,2-dimethoxyethane; water at 45℃; for 12h;
32% With ammonium cerium (IV) nitrate; 1-ethylene glycol monomethyl ether-3-methylimidazolium methanesulfonate; lithium chloride at 80℃; for 5h;
With tetrachloromethane; chlorine; acetic acid Hydrolysis.mit HCl enth. Methanol;
Multi-step reaction with 3 steps 1: pyridine; dmap / 4 h / 25 °C 2: ammonium cerium (IV) nitrate; lithium chloride / acetic acid; acetonitrile / 8 h / 80 °C 3: ammonia / methanol / 5 h
Multi-step reaction with 3 steps 1: pyridine / 20 °C / Inert atmosphere 2: ammonium cerium (IV) nitrate; lithium chloride / acetonitrile / 44 h / 80 °C 3: ammonium hydroxide / methanol / 20 °C

 

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