Abstract
AbstractThe synthesis of 5‐hydroxy‐2‐(β‐D‐ribofuranosyl)pyridine (12) from 2‐(2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranosyl)furan (1) is described. Treatment of 1 with α‐methoxycarbamate in the presence of p‐toluenesulfonic acid in benzene at reflux temperature afforded furfurylcarbamate (2) and its α‐isomer in a 5/1 ratio. The anomerization was circumvented by treatment of 1 with α‐methoxycarbamate in the presence of boron trifluoride in benzene at room temperature. Compound 2 was electrochemically oxidized to give dihydrofuran 4. However, conversion of 4 into 11 was unsuccessful. Treatment of azide 8 with bromine and methanol afforded 9. Reduction of 9 with zinc powder gave dihydrofurfurylamine 10, in 80% yield. Treatment of this with concentrated hydrochloric acid in methanol yielded 11, which on deblocking with 5% sodium hydroxide aqueous solution gave 12.
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