Taisuke Itaya

A simple synthesis of 3-β-D-ribofuranosylwye and the stability of its glycosidic bond

Treatment of 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide (3) with CNBr followed by cyclization and reaction with bromoacetone gave 3-β-D-ribofuranosylwye (2) whose glycosidic bond was cleaved rapidly in acidic or alkaline solution, but was fairly stable at pH 5–8·5 at 37 °C.

Hydrolysis of nucleosides related to wyosine

The glycosidic bond of 3-β-D-ribofuranosylwye (1) has been found to undergo not only hydrogen ion catalysed cleavage but also general base catalysed or nucleophilic cleavage; steric assistance has been shown to account for its unusual susceptibility to acid.

Synthesis of 3,9-dimethyl- and 3-methyl-9-ethyl-adenine via N′-alkoxy-1-alkyl-5-formamidoimidazole-4-carboxamidine

3,9-Dimethyl- and 3-methyl-9-ethyl-adenine have been synthesized from N′-alkoxy-1-alkyl-5-formamidoimidazole-4-carboxamidine (II) by reduction with LiAIH4 followed by cyclisation with ethyl orthoformate and removal of the alkoxy-group by catalytic hydrogenolysis.

Oxidation of N6-benzyladenine with m-chloroperoxybenzoic acid: formation of the N(1)-oxide

Oxidation of N 6 -benzyladenine (2) with m-chloroperoxybenzoic acid in MeOH has been found to give N 6 -benzyladenine 1-oxide (1) as the main product. The structure of 1 has been established by leading it to N 6 -methoxyadenine (4) though O-methylation, Dimroth rearrangement, and nonreductive debenzylation