The synthesis of [([beta-D-ribofuranosyloxy)methyl]nucleosides
Hari Babu Mereyala1, Sreeman Kumar Mamidyala
1Gas Based Chemicals and Processes Division, Indian Institute of Chemical Technology, Tarnaka, Hyderabad, India. mereyalahb@rediffmail.com
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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