Synthesis of β-d-Galp-(1→4)-α-d-Manp methanephosphonate, a substrate analogue for the elongating α-d-mannosyl phosphate transferase in the Leishmania

An isosteric C-glycoside phosphono analogue of dec-9-enyl β-d-galactopyranosyl-(1→4)-α-d-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner–Emmons/Michael reaction was developed for the stereoselective preparation of α-d-mannosyl methanephosphonate derivatives.