Structure of (±)-1,2;4,5-di-O-cyclohexylidene myo-inositol and synthesis of myo-inositol 3-phosphate via its phosphorylation with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one

The crystal structure of (±)-1,2;4,5-di-O-cyclohexylidene myo-inositol, refined to R = 2.9%, shows interestingly disordered (flip-flop) hydrogen bonding. The higher reactivity of the 1/3 positions (rather than 4/6) has been evaluated using semi-empirical calculations. This diol has been phosphorylated with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one and the diastereoisomer derived from phosphorylation at the 3-position was isolated by crystallisation. Deprotection with TFA/H2O then H2/Pd-C afforded myo-inositol 3-phosphate in only four steps from myo-inositol.