Synthesis and Biological Evaluation of (2-Hydroxyethyl) 2-Deoxy-α-D-Threo-Pyranoside 3,4,2′-Trisphosphate,A Mimic of the Second Messenger Inositol 1,4,5-Trisphosphate

ABSTRACT

(2-Hydroxyethyl) 2-deoxy-α-D-threo-pentopyranoside 3,4,2′-trisphosphate (3) has been prepared starting from allyl-α-D-xylopyranoside. The suitably protected 2-deoxy intermediate obtained by judicious selective protection and deprotection has been phosphorylated using the phosphoramidite methodology. Final deprotection gave the expected analogue of myo-inositol 1,4,5-trisphosphate.