Chemical synthesis of allyl-[~13C_6]-glucuronate

摘要

The synthesis of allyl-[~13C_6]-glucuronate from alpha-D-[~13C_6]-glucose in five steps is described. Selective protection of the primary alcohol in the glucose with the bulky trityl group followed by acetylation in the same pot gave the fully protected sugar. Removal of the trityl group followed by oxidation of the primary alcohol to the acid and removal of the acetate groups using catalytic amounts of sodium methoxide gave the glucuronic acid. Reaction with allyl bromide using resin-bound fluoride gave the title compound.