RAPID SYNTHESIS OF 2-DEOXY-D-(1-C-14) GLUCOSE SUITABLE FOR LABELING WITH C-11

D‐arabitol (I) treated with acetone gave 2,3–4,5 and 1,2–4,5 di‐O‐isopropylidene‐D‐arabitol (II) as shown by 13C NMR. This mixture was converted into the corresponding mixture of mesylates from which 2,3–4,5‐di‐0‐isopropylidene‐1–0‐methane sulfonyl‐D‐arabitol (III) was isolated. The latter was converted into 1‐deoxy‐2,3–4,5‐di‐O‐isopropylidene‐1‐iodo‐D‐arabitol (IV). (IV) and sodium (14C) cyanide gave 2‐deoxy‐3,4–5,6‐di‐0‐isopropylidene‐D‐(1‐14C)‐glucononitrile (V) which was hemihydrogenated into 2‐deoxy‐D‐(1‐14C)‐glucose (VI). The overall yield based on sodium‐(14C)‐cyanide was 30 % and the radiochemical purity was 98 %. The overall time of synthesis was about one hour. This is suitable for working with 20 minutes halflived 11C. Copyright © 1979 John Wiley & Sons, Ltd.