161972-49-2

Upstream product

• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 87-89-8 D-myo-inositol 
• 115072-68-9 racemic 1,4-di-O-allyl-myo-inositol 
• 99756-37-3 (±)-3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 98906-32-2 (±)-1,4-di-O-allyl-2,3:5,6-di-O-isopropylidene-myo-inositol 

Downstream Products

• 114419-08-8 (+)-1L-2,5,6-tri-O-benzyl-myo-inositol 
• 6195-45-5 (+)-2,3,4,5,6-pentakis-O-benzyl myo-inositol 
• 114419-09-9 (-)-1L-2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-myo-inositol 
• 140886-99-3 Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6R)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester 

Relevant academic research and scientific papers

Unambiguous Total Synthesis of the Enantiomers of myo-Inositol 1,3,4-Trisphosphate: 1L-myo-Inositol 1,3,4-Trisphosphate Mobilizes Intracellular Ca2+ in Limulus Photoreceptors

Syntheses of the enantiomers of myo-inositol 1,3,4-trisphosphate are described. 1,4-Di-O-allyl-myo-inositol was regioselectively p-methoxybenzylated at the 3-position to give 1,4-di-O-allyl-3-O-(p-methoxybenzyl)-myo-inositol followed by benzylation of the remaining free hydroxyl groups to give the key intermediate 1,4-di-O-allyl-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol.Removal of the p-methoxybenzyl and allyl groups gave 2,4,5-tri-O-benzyl-myo-inositol which was-phosphitylated with bis(benzyloxy)(diisopropylamino)phosphine to give the fully protected trisphosphite triester.Oxidation using tert-butyl hydroperoxide gave 2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-myo-inositol, and deprotection using sodium in liquid ammonia gave racemic myo-inositol 1,3,4-trisphosphate.Deprotection of the key intermediate 1,4-di-O-allyl-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol by isomerization of allyl groups followed by mild acid hydrolysis gave 2,4,5-tri-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol, which was converted to the diastereoisomeric bis-(-)-camphanates.The diastereoisomers were separated by column chromatography and the camphanates and the p-methoxybenzyl group removed by saponification and acid hydrolysis, respectively, for each diastereoisomer to give the enantiomers of 2,4,5-tri-O-benzyl-myo-inositol.The absolute configurations of the latter were established by conversion of 1L-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol to the known 1L-1,2,4,5,6-penta-O-benzyl-myo-inositol.Phosphorylation and deblocking gave the D- and L-enantiomers of myo-inositol 1,3,4-trisphosphate.Biological evaluation in Limulus photoreceptors showed that 1L-myo-inositol 1,3,4-trisphosphate was much more active than the D-enantiomer, producing repetitive bursts of depolarization due to mobilization of intra cellular calcium.