Divergent synthesis of all possible optically active regioisomers of Myo-inositol mono- and bisphosphates

Abstract

All possible optically active regioisomers of myo- inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IR(n)s) as key intermediates. A series of procedures including Novozym 435 catalyzed enzymatic resolution of (3aR, 4S, 7S, 7aR)-rel-3a, 4,7,7a-tetrahydro- 2,2-dimethyl- 1,3- benzodioxole-4,7- diol diacetate, several protection and deprotection reactions, and acyl migration afforded two enantiomeric pairs of IR5 and six enantiomeric pairs of IR4. Phosphorylation of these key intermediates by the phosphitylation and oxidation procedure gave the target products after removal of the protecting groups. [GRAPHICS]