Synthesis
The general procedure for the synthesis of (3R,4R,5R)-5-(acetyloxymethyl)tetrahydrofuran-2,3,4-triyl triacetate from the compound (CAS:532-20-7) and ethanoic anhydride was carried out as follows: peroxoacetylation of natural carbohydrates was carried out according to the literature procedure under the catalysis of pyridine with appropriate modifications. A mixture of carbohydrate (1.0 mmol), ethanoic anhydride (1.9 mL; 20 mmol) and pyridine (3 mL) was stirred and reacted at 25°C for 24 hours. After completion of the reaction, the reaction mixture was diluted with 5 mL of dichloromethane, and the organic phase was washed sequentially with 1 mol/L hydrochloric acid (3 × 5 mL), saturated sodium bicarbonate solution (3 × 5 mL), and brine (5 mL). The organic layer was dried with anhydrous sodium sulfate and subsequently concentrated under reduced pressure to afford the fully-O-acetylated carbohydrate derivative. The structures of the resulting fully acetylated carbohydrates were in agreement with those reported in the literature through physical properties and spectroscopic data.
References
[1] Tetrahedron Letters, 2008, vol. 49, # 29-30, p. 4491 - 4493
[2] European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 2713 - 2718
[3] Asian Journal of Chemistry, 2014, vol. 26, # 14, p. 4367 - 4369
[4] Journal of the Brazilian Chemical Society, 2015, vol. 26, # 4, p. 755 - 764
[5] Organic and Biomolecular Chemistry, 2004, vol. 2, # 17, p. 2538 - 2546
