Purine nucleosides. Part XXXII. Synthesis and reactivity of 6-alkyl-seleno-9-(β-D-ribofuranosyl)purines
Abstract
The alkylation of 6-selenoxo-9-(β-D-ribofuranosyl)purine with several alkyl halides under basic conditions has furnished the corresponding 6-alkylseleno-9-(β-D-ribofuranosyl)purines. A ready removal of the 6-methylseleno-group from the 6-methylseleno-derivative (3) with Raney nickel under mild conditions has furnished an almost quantitative yield of nebularine. Treatment of the 6-benzylseleno-derivative (4) with nucleophilic reagents has demonstrated the ease of displacement of the alkylseleno-group.