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ChemicalBook CAS DataBase List 5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine
23669-79-6

5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine synthesis

7synthesis methods
2'-Deoxyuridine

951-78-0

4,4'-Dimethoxytrityl chloride

40615-36-9

5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine

23669-79-6

To a solution of 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (22.80 g, 99.91 mmol) in anhydrous pyridine (200 mL) was added 4,4'-bis(methoxytrityl)chlorine (37.24 g, 109.90 mmol) and the mixture was allowed to stand at 25 °C for 12 hours. Upon completion of the reaction, the reaction was quenched with saturated NaHCO3/NH4Cl solution (200 mL) and subsequently extracted with ethyl acetate (3 x 200 mL). The organic layers were combined, washed with brine (2 x 100 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether: ethyl acetate, 2:1 to 0:1) to afford the target product 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (43.00 g, 72.94 mmol) as yellow foam.

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Yield:23669-79-6 99%

Reaction Conditions:

with pyridine for 3 h;Ambient temperature;

References:

Avino, Anna;Garcia, Ramon Gueimil;Albericio, Fernando;Mann, Matthias;Wilm, Matthias;Neubauer, Gitte;Eritja, Ramon [Bioorganic and Medicinal Chemistry,1996,vol. 4,# 10,p. 1649 - 1658]

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