2‐(1‐Isopropylidene)azino‐3‐β‐D‐ribofuranosyl‐5‐ methoxycarbonylmethylenethiazolidin‐4‐one (IV) and 2‐(1‐methylbenzilidene)azino‐3‐β‐D‐ribofuranosyl‐5‐carboxymethylenethiazolidin‐4‐one were prepared by independent synthesis utilizing either acid catalyzed fusion of 2‐(1‐isopropylidene)azino‐5‐methoxycarbonylmethylenethiazolidin‐3(H)‐4‐one (II) with 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranose, silylation procedure with 2,3,5‐tri‐O‐benzoyl‐D‐ribofuranosyl bromide or by cyclization of new isopropylidene and/or methylbenzilidene derivatives (VII) of 4‐(2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranosyl)thiosemicarbazide (VI) with maleic anhydride and subsequent methylation. The synthetic approach has unambigously established the glycosilation site as well as anomeric configuration, which was additionally derived from pmr spectral data.
Die Aminierung des Dihydrothiouridins (II) in Methanol liefert unter gleichzeitiger Desacetylierung das ungeschützte Dihydrocytidin (I), während in Dioxan nur die Verbindung (III) entsteht.
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