A general procedure for the preparation of labeled l-ascorbic acid from labeled d-glucose

A simple, three-step conversion of 1,2-O-isopropylidene-α-d-glucofuranose into l-ascorbic acid, originally described by Bakke and Theander, was used to prepare l-[4-¹⁴C]ascorbic acid from milligram amounts of d-[3-¹⁴C]glucopyranose in 28% radioisotopic yield. In addition, l-[6-¹⁴C]- and l-[U-¹⁴C]-ascorbic acid were prepared from d-[1-¹⁴C]- and d-[U-¹⁴C]-glucopyranose, respectively. The procedure is useful for the synthesis of l-ascorbic acid bearing isotopic hydrogen, carbon, or oxygen atoms at specific positions, subject only to the availability of starting material.