N6,N6-dibenzoyl-3',5'-O-dibenzoyl-2'-deoxyadenosine synthesis

Yield:105791-57-9 93%

Reaction Conditions:

with pyridine at 80; for 4 h;Time;

Steps:

4.2. N,N-Dibenzoyl-3′,5′-dibenzoyl-2′-deoxyadenosine (5)

Benzoyl chloride (6.29 g, 44.74 mmol) was added dropwise to a suspensionof 2′-deoxyadenosine (2.00 g, 7.99 mmol) in pyridine (20 mL) at 0 °C. Tocomplete the reaction, the mixture was stirred and heated to 80 °C for4 h. Then the solvent was removed in vacuo. The resulting residue wasdissolved in CH2Cl2 (100 mL) and washed with H2O (100 mL). The aqueouslayer was extracted with CH2Cl2 (3 × 50 mL). The combined organic layerswere washed with brine (100 mL), dried on anhydrous Na2SO4 and concentratedin vacuo. The resulting residue was recrystallized from EtOH togive 5 (3.84 g, 72% yield) as a white solid.

References:

Xia, Ran;Chen, Lei-Shan;Xu, Shao-Hong;Xia, Chao;Sun, Li-Ping [Nucleosides, nucleotides and nucleic acids,2022,vol. 41,# 7,p. 593 - 604]