455268-40-3

Upstream product

• 165883-87-4 L-1,6-di-O-benzoyl-myo-inositol 
• 454199-95-2 L-1,2,6-tri-O-benzoyl-3,4-O-isopropylidene-myo-inositol 
• 454200-06-7 L-1,6-di-O-benzoyl-3,4-O-isopropylidene-myo-inositol 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 455268-36-7 L-1,2,6-tri-O-benzoyl-myo-inositol 

Relevant academic research and scientific papers

Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates

Since the discovery of D-myo-inositol 1,4,5-trisphosphate, which plays a pivotal role as a second messenger in transmembrane signaling, the scope of the phosphoinositide-based signaling processes has been continually expanding. However, the clear understanding of the molecular signal transduction mechanisms including the functions of newly found IPn is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myoinositol phosphates (IPn; n = 1-6), we synthesized all possible optically active regioisomers of myo-IP3 and myo-IP4 using chiral IBz3s and IBz2s, respectively. A series of procedures involving CRL-catalyzed enzymatic resolution of racemic 1,2:5,6-di-O-isopropylidene-myo-inositol and base-catalyzed benzoyl migration in tri- and dibenzoyl-isopropylidene-myo-inositol afforded eight enantiomeric pairs of IBz3 and six enantiomeric pairs of IBz2, respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.