140886-99-3

Upstream product

• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 114419-08-8 (+)-1L-2,5,6-tri-O-benzyl-myo-inositol 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 114297-91-5 1D-(-)-1,2,4-tri-O-benzyl-myo-inositol 
• 98925-54-3 (+)-1,3,4-tri-O-allyl-2,5,6-tri-O-benzyl-myo-inositol 
• 136986-26-0 rac-1,3,4-Tri-O-allyl-5,6-O-isopropylidene-myo-inositol 
• 100-39-0 benzyl bromide 
• 161972-49-2 (-)-1L-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol 
• 115072-68-9 racemic 1,4-di-O-allyl-myo-inositol 
• 98906-32-2 (±)-1,4-di-O-allyl-2,3:5,6-di-O-isopropylidene-myo-inositol 
• 99756-37-3 (±)-3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 87-89-8 D-myo-inositol 
• 98906-30-0 (±)-2,3,6-tri-O-benzyl-myo-inositol 
• 67746-43-4 dibenzyl N,N-diethylphosphoramidite 

Downstream Products

• 114419-09-9 (-)-1L-2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-myo-inositol 
• 114342-70-0 1D-1,2,4-Tri-O-benzyl-myo-inositol 3,5,6-tris(dibenzyl phosphate) 
• 141116-53-2 C₄₈H₄₈O₁₅P₃^(3-)*3Na⁽¹⁺⁾ 
• 114342-70-0 Phosphoric acid dibenzyl ester (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphoryloxy)-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.

The preparation, resolution, and phosphorylation of some benzyl ethers of myo-inositol: Intermediates for the synthesis of myo-inositol phosphates of the phosphatidylinositol cycle

The syntheses of the following chiral compounds are described: 1D-2,3,6-tri-, 1D-2,4,5-tri, 1D-2,5,6-tri-, 1D-1,2,3,4-tetra, 1D-1,2,3,6-tetra-, 1D-1,2,4,5-tetra-, and 1D-2,3,5,6-tetra-0-benzyl-myo-inositol; and 1D-2,5,6-tri-0-benzyl-1-0-p-methoxybenyl- an