1-O-Acetyl-2,3,5-tri-O-benzoyl-b-D-ribofuranose is a key intermediate in the synthesis of ribonucleosides, purine, pyrimidine, and related nucleosides. Could anyone provide me with the method for its synthesis as it's very expensive for our lab?
"1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose was synthesized using D-ribose as starting material through methylation, benzoylation and acetylization. Effects of ratio of reactants, reaction time and reaction temp. on yield of the product were studied in detail. The optimal reaction conditions were obtained as follows: 5.0 g (0.033 mol) D-ribose was dissolved in 20 mL HCl/MeOH, followed by stirring the soln. at 20°C for 3 h. The reaction product was dissolved in 50 mL pyridine, then 15 mL (0.129 mol) benzoyl chloride was added, followed by stirring the soln. at 10°C for 15 h. The product was dissolved in a mixt. of 40 mL glacial acetic acid and 5 mL (0.083 mol) acetic anhydride, then 3 mL oil of vitriol was added, the soln. was stirred at 10°C for 15 h to get the final product. By means of the above process, the total yield of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-O-ribofuranose was up to 74.34% (HPLC purity: 98.1%)." See
---Deng, Yan; Tao, Deliang; Zhang, Yongqiang; Xie, Weiyue, Jingxi Huagong Zhongjianti (2009), 39(5), 30-33. | Language: Chinese
Good luck
First you should prepare the methyl glycoside (MeOH, H+ cat); then you benzoylate (BzCl, base); next you should remove the methyl group (Stir on silica in the presence of wáter) and finally acetylate (Ac2O, bas). Good luck!!!
- Badges
- Science topic
- Similar topics
- Chemistry
- Organic Chemistry