The synthesis of 3-(/3-D-ribofuranosyl)phthalimide ( 19) from 2-(2,3,5-tri-0-benzoyl-/3-D-ribofuranosyl)furan (1) is described. One sequence started by aromatizing Diels-Alder reaction adduct 2 to dimethyl l-(2,3,5-tri-0benzoyl-|8-D-ribofuranosyl)phthalate ( 3) with titanium tetrachloride-lithium aluminum hydride. Treatment of this with sodium hydroxide solution followed by dehydration with acetic anhydride and trifluoroacetic acid gave 3-(2,3,5-tri-0-acetyl-/3-D-ribofuranosyl)phthalic anhydride (12). However, conversion of 12 into the phthalimide C-nucleoside was unsuccessful. The second sequence, which was brought to completion, made use of the adduct 1-(2,3,5-tri-0-benzoyl-/3-D-ribofuranosyl)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboximide (17) as the starting material.
2‐Chlormercuri‐furan (II) reagiert mit dem Furanosylbromid (I) zu den Anomeren (III) und (IV), die mit Trifluoressigsäure zu (III) epimerisiert werden.
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