Stereoselective synthesis of the isosteric bisphosphono analogue of β-D-fructose 2,6-bisphosphate

Abstract

The isosteric bisphosphono analogue 2 of β-D-fructose 2,6-bisphosphate has been synthesized exploiting the C-fructofuranoside 5, the free hydroxy group of which was converted into phosphonate via iodide; the methylphosphonic group at C-6 was introduced by Witti–Horner reaction of the aldehyde 9, prepared by selective deprotection and oxidation of the hydroxy group at C-6.