Synthesis of 1-chiro-inositol-1,2,3-trisphosphate and -1,2,3,5-tetrakisphosphate by Ferrier reaction of methyl alpha-D-mannopyranoside

Abstract

The Ferrier rearrangement of a methyl alpha-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 (alpha-trinositol) and D-myo-inositol 1,3,4,5-tetrakisphosphate, respectively, and should be useful for the binding studies with their macromolecular counterparts. Copyright (C) 1996 Elsevier Science Ltd