111446-91-4

Basic information

• Product Name: (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol
• CAS NO: 111446-91-4
• Molecular Weight: 490.596
• Mol File: 111446-91-4.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol(111446-91-4)
• EPA Substance Registry System: (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol(111446-91-4)

Safety Data

• Hazardous Substances Data: 111446-91-4(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 35949-67-8 (±)-1,4-di-O-benzyl-myo-inositol 
• 114218-20-1 (+/-)-3-O-allyl-1,4-di-O-benzyl-myo-inositol 
• 98925-52-1 (+/-)-5,6-di-O-allyl-1,4-di-O-benzyl-myo-inositol 
• 58706-20-0 (+/-)-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 98906-25-3 (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 
• 98906-32-2 (±)-1,4-di-O-allyl-2,3:5,6-di-O-isopropylidene-myo-inositol 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 98906-30-0 (±)-2,3,6-tri-O-benzyl-myo-inositol 
• 77-76-9 2,2-dimethoxy-propane 
• 115072-72-5 2,3,6-tri-O-benzyl-4,5-isopropylidene-1-O-(prop-1-enyl)-myo-inositol 
• 98906-30-0 (+/-)-2,5,6-tri-O-benzyl-myo-inositol 
• 111446-91-4 (+/-)-1,6-O-isopropylidene-2,4,5-tri-O-benzyl-myo-inositol 

Downstream Products

• 115510-58-2 (+)-1D-2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-myo-inositol 
• 108340-81-4 L-myo-inositol 1,3,4-trisphosphate hexasodium salt 
• 108340-81-4 D-myo-inositol 1,3,4-trisphosphate hexasodium salt 
• 114419-09-9 (-)-1L-2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-myo-inositol 
• 114419-08-8 (+)-1L-2,5,6-tri-O-benzyl-myo-inositol 
• 120143-61-5 (3aR,4R,5R,6R,7S,7aR)-4,6,7-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-ol 
• 111446-91-4 (3aR,4R,5S,6R,7S,7aR)-4,6,7-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-ol 
• 111446-91-4 (3aS,4S,5R,6S,7R,7aS)-4,6,7-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-ol 
• 120143-62-6 (3aS,4S,5S,6S,7R,7aS)-4,6,7-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-ol 
• 114218-28-9 (3aS,4S,6S,7R,7aR)-4,6,7-Tris-benzyloxy-2,2-dimethyl-tetrahydro-benzo[1,3]dioxol-5-one 
• 114218-28-9 (3aR,4R,6R,7S,7aS)-4,6,7-Tris-benzyloxy-2,2-dimethyl-tetrahydro-benzo[1,3]dioxol-5-one 
• 484-68-4 1-O-methyl-myo-inositol 
• 80971-02-4 (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol 
• 114218-17-6 (+/-)-4,5-di-O-acetyl-1-O-allyl-2,3,6-tri-O-benzyl-myo-inositol 

Relevant articles and documents

Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation

O-Alkylation of myo-inositol derivatives containing more than one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results presented in this article as well as those available in the literature suggests that chelation of metal ions by inositol derivatives plays a significant role in the observed regioselectivity. Steric factors associated with the axial or equatorial disposition of the reacting hydroxyl groups do not contribute much to the outcome of these O-alkylation reactions. These results could serve as guidelines in planning synthetic strategies involving other carbohydrates and their derivatives.

A more convenient and general procedure for O-monobenzylation of diols via Stannylenes: A critical reevaluation of the Bu2SnO method

A more consistent, straightforward, and economical protocol for generation of stannylene species and their reaction with BnBr leading to products of O-monobenzylation of diols has been set. It has shown to be specially indicated for substrates bearing vicinal trans 1,2-diol moieties on cyclohexane backbones, which are more resistant to these transformations. Such protocol has been successfully applied to myo-inositol derivatives and acyclic diols.

The alkylation of dibutylstannylene derivatives of 1,2-O-isopropylidene-myo-inositol

Benzylation (or allylation) of 1,2-O-isopropylidene-myo-inositol in the presence of an excess of dibutyltin oxide gives, as major products, the readily isolable 3,4,6- (12) and 3,5,6-tri-O-alkyl (13) derivatives which are valuable intermediates for the synthesis of inositol phosphates of the phosphates of the phosphatidylinositol cycle.