Hydrogen Bromide → [(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)oxolan-2-yl]methyl benzoate

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Reaction Steps

Moreover, 2',3'-dideoxy-uridine or the derivatives thereof being the raw materials can be obtained easily from uridine being a constituting ingredient of ribonucleic acid by known method. For example, in the method described in Chem. Pharm. Bull., 18(3), 554-560, 1970, uridine is treated with methanesulfonyl chloride in pyridine solvent to convert to 2',3',5'-tri-O-methanesulfonyluridine and, by allowing this to react with sodium benzoate in acetamide or dimethylformamide solvent, 2,2'-anhydro-1-(5'-O-benzoyl-3'-O-mesyl-β-arabinosyl)uracil is obtained. This is allowed to react with hydrogen bromide or acetyl bromide to convert to 5'-O-benzoyl-2'-bromo-2'-deoxy-3'-O-mesyluridine and then this is treated with palladium carbon or Raney nickel catalyst in ethanol under atmosphere of hydrogen to obtain 5'-O-benzoyl-2',3'-dideoxy-uridine in a yield of about 60% (Chem. Pharm. Bull., 18(3), 554-560, 1970).

Provenance & Evidence