(2-Hydroxyethyl)-α-D-glucopyranoside-2′,3,4-trisphosphate: synthesis of a second messenger mimic related to adenophostin A

Abstract

A concise synthetic route from D-glucose to a chiral, biologically active, phosphorylated analogue of the highly potent Ca²⁺-mobilising agonist adenophostin A has been developed, involving a regioselective dibenzylation of allyl α-D-glucopyranoside and a one-pot Lemieux-type allyl oxidation with subsequent reduction and neighbouring deketalisation, to provide the key intermediate for phosphorylation.