Synthesis of L- chiro-inositol-1,2,3-trisphosphate and -1,2,3,5-tetrakisphosphate by ferrier reaction of methyl α-D-mannopyranoside

Abstract

The Ferrier rearrangement of a methyl α- d-mannopyranoside derivative (8a), followed by a stereoselective reduction gave a l -chiro- inositol derivative (2), which was converted to l -chiro- inositol 1,2,3-trisphosphate (3) and l -chiro- inositol 1,2,3,5-tetrakisphosphate ( 4). Compounds 3 and 4 may be considered to be the C3-position stereoisomers of d -myo- inositol 1,2,6-trisphosphate (α-trinositol) and d -myo- inositol 1,3,4,5-tetrakisphosphate, respectively, and should be useful for the binding studies with their macromolecular counterparts.