A novel chemical synthesis of a 3-deoxy-D-arabino-heptulosonic acid 7-phosphate (DAHP) derivative and its 2-deoxy analogue

Using 2,3,4,6-tetra O-acetyl-beta-D-glucopyranosyl cyanide as a precursor, methyl (methyl 3-deoxy-alpha-D-arabino-hept-2-ulopyranosid)onate (6) and its 2-deoxy analogue (10) were prepared. The synthesis involved an elimination of one molecule of acetic acid from C-2-C-3 and transformation of the CN group into COOMe, followed by methoxymercuration with subsequent reductive removal of the mercuri residue to give 6 or hydrogenation of the double bond to give 10. Phosphorylation of the 7-OH group led to the title compounds. (C) 1996 Elsevier Science Ltd.