Aziridination Of The Uracil 5,6-Olefinic Bond Of 3-N-3',5'-Di-O-Tribenzoyl-5-Vinyl-2'-Deoxyuridine

Oxidation of N-aminophthalimide with lead tetra-acetate at - 50-degrees gives N-acetoxyaminophthalimide (3) which selectively aziridinates the 5,6-double bond present in 3-N-3',5'-di-O-tribenzoyl-5-vinyl-2'-deoxyuridine (1a) to yield 2-[1'-(2'-deoxy-beta-D-ribofuranosyl)]-7-(1-phthalimido)-4-N-3',5'-di-O-tribenzoyl-6-vinyl-2,4,7-triaza-bicyclo[4.1.0]heptan-3,5-dione (5).