Abstract
The coupling reaction of acetoxymethoxy ribofuranoside 4 with nucleic acid bases 5a–f to synthesize novel (ribofuranosyloxy)methyl uracil, thymine, cytosine, adenine, guanine derivatives 6a–g respectively in preference to the expected formation of natural nucleosides 2′,3′,5′‐tri‐O‐benzoyl uridine, methyluridine, cytidine, adenosine and guanosine 7a–g is described. Detailed study of these reactions catalysed by Lewis acids TMSOTf and SnCl4 is described. TMSOTf exhibited selectivity for the formation of ribofuranosyloxy methyl derivatives 6a–g rather than 7a–g. Reason for formation of 6a–g is explained by HSAB principle.
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