CHEMICAL SYNTHESIS OF D-XYLO-HEXOS-5-ULOSE 6-PHOSPHATE A PUTATIVE INTERMEDIATE IN BIOSYNTHESIS OF MYO-INOSITOL

The crystalline di(cyclohexylamine) salt of 1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose dimethyl acetal 6-phosphate (8) has been synthesized from 3-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-glucofuranose (1) by a series of steps involving structures 2 to 7. The major product of the acidic hydrolysis of 8 has been reduced to a two-component mixture, and one of the components there in has been shown to be glucitol 6-phosphate (10). Dephosphorylation of the two-component mixture gave iditol and glucitol. It is, therefore, concluded that the major product of the hydrolysis of 8 is D-xylo-hexos-5-ulose 6-phosphate (9), a postulated intermediate in the biosynthesis of myo-isonitol from D-glucose 6-phosphate. © 1968, American Chemical Society. All rights reserved.