The synthesis of [([beta-D-ribofuranosyloxy)methyl]nucleosides.
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.
Mereyala
Hari Babu
HB
Gas Based Chemicals and Processes Division, Indian Institute of Chemical Technology, Tarnaka, Hyderabad, India. mereyalahb@rediffmail.com
Mamidyala
Sreeman Kumar
SK
D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D012266:Ribose / Q000138:chemical synthesis* / Q000737:chemistry
D009705:Nucleosides; D012266:Ribose