111392-10-0

Basic information

• Product Name: 1,6:3,4-di-O-isopropylidene-2,5-di-O-p-methoxybenzyl-myo-inositol
• CAS NO: 111392-10-0
• Molecular Weight: 500.589
• Mol File: 111392-10-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,6:3,4-di-O-isopropylidene-2,5-di-O-p-methoxybenzyl-myo-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6:3,4-di-O-isopropylidene-2,5-di-O-p-methoxybenzyl-myo-inositol(111392-10-0)
• EPA Substance Registry System: 1,6:3,4-di-O-isopropylidene-2,5-di-O-p-methoxybenzyl-myo-inositol(111392-10-0)

Safety Data

• Hazardous Substances Data: 111392-10-0(Hazardous Substances Data)

Upstream product

• 87-89-8 D-myo-inositol 
• 142387-37-9 2,5-di-O-p-methoxybenzyl-myo-inositol 
• 77-76-9 2,2-dimethoxy-propane 
• 824-94-2 p-methoxybenzyl chloride 
• 142387-35-7 C₃₄H₄₄O₈ 
• 136986-12-4 1,3,4,6-tetra-O-allyl-myo-inositol 
• 99756-37-3 (±)-3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 

Downstream Products

• 111392-16-6 1,4,5-tri-O-allyl-2,3,6-tri-O-p-methoxybenzyl-myo-inositol 
• 111392-17-7 1,2,4-tri-O-p-methoxybenzyl-myo-inositol 
• 111392-13-3 1,4,5-tri-O-allyl-3,6-di-O-p-methoxybenzyl-myo-inositol 
• 111392-11-1 (3aR,4R,5S,6S,7R,7aS)-5,6-Bis-allyloxy-4,7-bis-(4-methoxy-benzyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 111392-12-2 5,6-di-O-allyl-1,4-di-O-p-methoxybenzyl-myo-inositol 
• 35949-67-8 (±)-1,4-di-O-benzyl-myo-inositol 
• 111420-50-9 DL-2,3-O-isopropylidene-1,4-di-O-p-methoxybenzyl-myo-inositol 

Relevant articles and documents

Regioselective functionalizations and conformational studies of di-O-isopropylidene-myo-inositol derivatives

(+/-)-1,2:4,5-Di-O-isopropylidene-myo-inositol (5) and (+/-)-1,2:5,6-di-O-isopropylidene-myo-inositol (6) could be regioselectively functionalized in reactions including alkylation, acylation, and silylation at HO-3 in preference to HO-6 and HO-4, respectively, under specific conditions.The presence of intramolecular hydrogen bonding was evident in IR and 1H NMR spectra, and the HO-3 group was identified as the hydrogen-bonding donor in 5 and 6.In their crystalline states, diol 5 prefers a chair conformation and diol 6 a twist boat (skew) conformation.Both compounds appear to have substantial populations of chair conformations in the gas and solution phases, on the basis of the MM-2 energy minimizations and comparisons of vicinal coupling constants observed in the 1H NMR spectra (in CDCl3 and Me2SO-d6) and calculated from the crystal and MM-2 conformations.It is suggested as an explanation for the observed selectivities that the kinetic acidity of the HO-3 group may be enhanced through its intramolecular hydrogen bonding with the cis-vicinal oxygen, or the nucleophilicity of the 3-alkoxide may be enhanced due to its interaction with the cis-vicinal oxygen in a manner similar to the through-space α-effect.

The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates

Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for 'temporary' protection.The benzyl ethers are required as intermediates for the synthesis of the 'second messenger', inositol 1,4,5-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.