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