Uridine, 2'-deoxy-5-[2-(trimethylsilyl)ethynyl]-, 3',5'-diacetate synthesis
- Product Name:Uridine, 2'-deoxy-5-[2-(trimethylsilyl)ethynyl]-, 3',5'-diacetate
- CAS Number:85267-60-3
- Molecular formula:C18H24N2O7Si
- Molecular Weight:408.48
1.Add DMAP (0.16 mmol, 20 mg) to a stirred suspension of 2'-deoxyuridine (1 mmol, 228 mg) in acetic anhydride (7.5 mL).2.Observe the reaction mixture become homogenous for 6 hours.3.Remove the volatiles in vacuum.4.Purify the residue by flash chromatography on silica gel eluted with EA/cyclohexane (4:1 → 19:1, v/v) to obtain 3',5'-di-O-acetyl-2'-deoxyuridine.
1956-30-5
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Yield:85267-60-3 86%
Reaction Conditions:
with copper(l) iodide;tetrakis(triphenylphosphine) palladium(0);triethylamine in N,N-dimethyl-formamide at 20; for 18 h;Inert atmosphere;Sonogashira coupling;
Steps:
4.1.3. General procedure for the synthesis of compounds 8b-16b
A mixture of 8a-16a (1.0 equiv), CuI (0.1 equiv) and Pd(PPh3)4 (0.05 equiv) in Et3N and DMF was degassed with Ar. Trimethylsilylacetylene (2.0 equiv) was then added and the solution was stirred for 18 h at room temperature under an Ar atmosphere. TLC analysis showed complete conversion of starting material to a major product. The reaction mixture was then cooled to room temperature, diluted with Et2O, washed twice with satd aq NH4Cl, dried over Na2SO4, filtered, and concentrated in vacuum. The crude product was purified by silica gel column chromatography to yield pure material.
References:
Li, Tiehai;Guo, Lina;Zhang, Yan;Wang, Jiajia;Li, Zhonghua;Lin, Lin;Zhang, Zhenxing;Li, Lei;Lin, Jianping;Zhao, Wei;Li, Jing;Wang, Peng George [Carbohydrate Research,2011,vol. 346,# 9,p. 1083 - 1092] Location in patent:experimental part
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![Uridine, 2'-deoxy-5-[[(trifluoromethyl)sulfonyl]oxy]- (9CI)](/CAS/20210305/GIF/151361-85-2.gif)
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85267-60-3
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951-78-0
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54-42-2
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