Prodrugs of vitamin C: the reaction of 1-acyloxyalkyl-1-iodides with vitamin C 5,6-acetonide

The reaction of 2 equiv of 1-acyloxyalkyl-1-iodides with vitamin C 5,6-acetonide gave mixtures of products that were O-alkylated on the 3-position and either O-alkylated, 7, or O-acylated, 8, on the 2-position. The 8 products comprised the majority of the mixtures: 56:54 to 94:6. The 3-alkylated-2-acylated prodrugs, 8, hydrolyzed to vitamin C 5,6-acetonide chemically at pH 7.4 with half-lives of 6-12 h.89