✍ Scribed by Laurence Mévellec; François Huet
No coin nor oath required. For personal study only.
Nucleoside analogue 7 was obtained by nucleophilic substitution between adenine and mesylate 5b. On the other hand the same reaction starting from its isomer 5a did not work and led to the surprising ring contraction products 8a and 8b. Another unexpected ring contraction leading to 15 was pointed out in the course of preparation of the deuteriated compounds 5a' and 5a". Position of deuterium in products 8a' and 8b' or 8a" and 8b" issued from reactions with 5a' or 5a" gave useful mechanistic informations on this reaction.
📜 SIMILAR VOLUMES
The synthesis of C-nucleosldes requires intermediates of type XIV, XVI2 , XVII or XVIII 3,4 which are as yet not too readily available. Olefin XIII held promrse as a precursor for such intermedrates and we therefore set out to synthesize It. Brcyclic acid I', obtarned by standard reactions from kn
## Abstract The synthesis of a novel ring‐expanded nucleoside analogue, (Z)‐1‐((2‐Guanidinocarbamoyl‐cyclopropylidene)methyl)‐4,5,7,8‐tetrahydro‐6__H__‐6‐iminoimidazo[4,5‐__e__][1,3]diazepine‐4,8‐dione (**1**) has been reported. It was prepared starting from methyl imidazole‐4,5‐dicarboxylate by se