Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside

Uses

Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].

Synthesis

12 g (73.1 mmol) of methyl ALPHA-D-xylofuranoside was placed in a 250 mL aubergine flask, 160 mL of analytically pure DMF was added, and 17 g of NaH (60% dispersed in mineral oil) was added in batches under ice bath cooling. Subsequently, 38 mL of benzyl bromide was slowly added dropwise, and after completion of the dropwise addition, the reaction was gradually warmed to room temperature and stirred overnight. The reaction was monitored by TLC. Upon completion of the reaction, the reaction was quenched by careful addition of methanol and then the reaction mixture was extracted with ethyl acetate (EA). The organic phase was washed three times with water, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (eluent: petroleum ether/ethyl acetate = 15:1 to 9:1) to afford the target compound (2R,4S)-3,4-bis(benzyloxy)-2-((phenylmethoxy)methyl)-5-methoxytetrahydrofuran (28.6 g, 65.8 mmol, 90% yield).

References

[1] Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88. DOI:10.2174/138161212801227005