ChemicalBook CAS DataBase List 3',5'-Bis-O-(triphenylMethyl)uridine

3',5'-Bis-O-(triphenylMethyl)uridine synthesis

4synthesis methods

Product Name:3',5'-Bis-O-(triphenylMethyl)uridine
CAS Number:4710-75-2
Molecular formula:C47H40N2O6
Molecular Weight:728.83

76-83-5 Synthesis

76-83-5
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$6.00/25g

58-96-8 Synthesis

58-96-8
641 suppliers
$5.00/1g

6554-10-5
62 suppliers
$28.60/50MG

4710-75-2
17 suppliers
$1066.00/1g

6554-11-6 Synthesis

6554-11-6
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Yield:6554-10-5 56% ，4710-75-2 8% ，6554-11-6 16%

Reaction Conditions:

in pyridine at 80;Inert atmosphere;

Steps:

4.2 Tritylated uridine analogues

Uridine (6) (1.1g, 4.4mmol) was coevaporated twice with dry pyridine and dissolved in dry pyridine (4.5mL/mmol). Triphenylmethyl chloride (2.8eq) was added and the solution was heated to 80°C overnight under argon. The reaction was quenched by adding methanol (3mL) at room temperature for 30min. The solution was then concentrated and diluted in dichloromethane. The organic solution was washed three times with a solution of saturated NaHCO₃ and the combined aqueous layers were extracted with dichloromethane. Combined organic layers were dried over Na₂SO₄, filtered and concentrated under vacuum. The residue was purified by column chromatography on silica (going from 20 to 0% hexane in dichloromethane containing 0.5% triethylamine, followed by 0-2.5% MeOH/ DCM and 0.5% triethylamine) and afforded the tritylated compounds 1a (1184mg, 2.43mmol, 56% yield), 1b (262mg, 0.36mmol, 8% yield) and 1c (517mg, 0.71mmol, 16% yield) as white foams.

References:

Chatelain, Grégory;Debing, Yannick;De Burghgraeve, Tine;Zmurko, Joanna;Saudi, Milind;Rozenski, Jef;Neyts, Johan;Van Aerschot, Arthur [European Journal of Medicinal Chemistry,2013,vol. 65,p. 249 - 255]

76-83-5 Synthesis

76-83-5
694 suppliers
$6.00/25g