193285-10-8

Upstream product

• 54750-12-8 (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one 
• 34361-60-9 1,2:4,5-dicyclohexylidene-myo-inositol 

Downstream Products

• 14980-89-3 D-myo-inositol-3-phosphate biscyclohexylamine salt 
• 193285-11-9 Phosphoric acid (1R,2S)-2-methylamino-1-phenyl-propyl ester (1S,2S,3R,4S,5S,6S)-2,3,4,5,6-pentahydroxy-cyclohexyl ester 

Relevant academic research and scientific papers

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.