Abstract
A simple synthesis of tubercidin (1), 7-deazaguanosine (2) and 2′-deoxy-7-deazaguanosine (14) has been accomplished using the sodium salt glycosylation procedure. Reaction of the sodium salt of 4-chloro- and 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine, 3 and 4, respectively, with 1-chloro-2,3-0-isopropylidene-5-0-(t-butyl)dimethylsilyl-α-D-ribofuranose (5) gave the corresponding protected nucleosides 6n and 7 with β-anomeric configuration. Deprotection of 6 provided 8, which on heating with methanolic ammonia gave tubercidin (1) in excellent yield. Functional group transformation of 7, followed by deisopropylidenation gave 2-aminotubercidin (10) and 2-amino-7-β-D-ribofuranosylpyrrolo[2,3-d]pyrimidine-4(3H)-thione (11). Treatment of 7 with 1N sodium methoxide followed by exposure to aqueous trifluoroacetic acid, and ether cleavage furnished 7-deazaguanosine (2). 2′-Deoxy-7-deazaguanosine (14) and 2′-deoxy-7-deaza-6-thioguano-sine (18) were also prepared by using similar sequence of reactions employing 4 and 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose (15).
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