115116-22-8

Basic information

• Product Name: 3,4,5,6-TETRAKIS(BENZYLOXY)-1,2-CYCLOHEXANEDIOL
• Synonyms: 3,4,5,6-TETRAKIS(BENZYLOXY)-1,2-CYCLOHEXANEDIOL;TETRABENZYLIC MYO-INOSITOL;TETROBENZYLIC MYO-INOSITOL
• CAS NO: 115116-22-8
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.65
• Mol File: 115116-22-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 167-169 °C
• Boiling Point: 665.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.24±0.1 g/cm3(Predicted)
• PKA: 12.79±0.70(Predicted)
• CAS DataBase Reference: 3,4,5,6-TETRAKIS(BENZYLOXY)-1,2-CYCLOHEXANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,6-TETRAKIS(BENZYLOXY)-1,2-CYCLOHEXANEDIOL(115116-22-8)
• EPA Substance Registry System: 3,4,5,6-TETRAKIS(BENZYLOXY)-1,2-CYCLOHEXANEDIOL(115116-22-8)

Safety Data

• Hazardous Substances Data: 115116-22-8(Hazardous Substances Data)

Usage

Uses

Tetrobenzylic Myo-inositol is used as a reactant in the synthesis of differentially substituted silyloxy myo-inositol derivatives.

Upstream product

• 131147-02-9 (+/-)-1,6-di-O-allyl-3,4,5-tri-O-benzyl-myo-inositol 
• 131147-11-0 (±)-2,3-O-isopropylidene-1,5,6-tri-O-benzyl-4-O-allyl-myo-inositol 
• 131146-91-3 (+/-)-4-O-allyl-1,5,6-tri-O-benzyl-myo-inositol 
• 58706-24-4 (±)-3-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 131146-99-1 (+/-)-2,3,4-tri-O-allyl-1,5,6-tri-O-benzyl-myo-inositol 
• 131146-92-4 (+/-)-1,5,6-tri-O-benzyl-4-O-(prop-1-enyl)-myo-inositol 
• 131147-01-8 (+/-)-1,6-di-O-allyl-4,5-di-O-benzyl-2,3-O-isopropylidene-myo-inositol 
• 116786-69-7 (+/-)-1,6-di-O-allyl-4,5-di-O-benzyl-myo-inositol 
• 131146-96-8 (+/-)-1,2,6-tri-O-allyl-3-O-benzyl-4,5-O-isopropylidene-myo-inositol 
• 131146-87-7 (±)-4-O-allyl-1-O-benzyl-2,3;5,6-di-O-isopropylidene-myo-inositol 
• 131146-97-9 (1S,2S,3R,4S,5R,6R)-3,4,5-Tris-allyloxy-6-benzyloxy-cyclohexane-1,2-diol 
• 131146-95-7 (+/-)-1,6-di-O-allyl-3-O-benzyl-4,5-O-isopropylidene-myo-inositol 
• 131146-94-6 (+/-)-1,6-di-O-allyl-3-O-benzyl-myo-inositol 
• 131146-88-8 (±)-4-O-allyl-1-O-benzyl-2,3-O-isopropylidene-myo-inositol 

Downstream Products

• 131233-74-4 2-O,3-O,4-O,5-O-tetrabenzyl-L-myo-inositol 
• 141040-41-7 (+/-)-1,2,3,4-tetra-O-benzyl myo-inositol 
• 141116-52-1 (+/-)-1,2,3,4-Tetra-O-benzyl-myo-inositol 5,6-bis(disodium phosphate) 
• 109545-46-2 (+/-)-1,2,3,4-Tetra-O-benzyl-myo-inositol 5,6-bis 
• 115432-19-4 (+/-)-1,2,3,4-Tetra-O-benzyl-myo-inositol 5,6-bis(dinbenzyl phosphate) 
• 24558-77-8 3,4,5,6-tetra-O-benzyl inositol 
• 29847-13-0 (3aR,4S,5R,6S,7S,7aR)-4,5,6,7-Tetrakis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 110550-27-1 (1S,2R,3R,4S)-cyclohex-5-ene-1,2,3,4-tetrayltetrakis(oxy)tetrakis(methylene)tetrabenzene 

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.

Stable axial-rich chair conformer of myo-inositol derivatives due to introduction of two adjacent bulky silyl protections

The ring-conformational change of myo-inositol derivatives by introducing two tert-butyldimethylsilyl, triisopropylsilyl, or tert-butyldiphenylsilyl groups into the 1,2-trans hydroxy groups - 3,4- and 4,5-positions - were investigated. The cyclohexane cores of the 4,5-bis-O-silylated derivatives with tert-butyldiphenylsilyl or triisopropylsilyl groups were present in the axial-rich chair form.

Total synthesis of myo-inositol polyphosphates from benzene via conduritol B derivatives

The four (±)-myo-inositol phosphates 1,4,5-IP3 (1), 2,4,5-IP3 (15), 1,2,4,5-IP4 (17) and 4,5-IP2 (19) have been synthesised from benzene, using the protected conduritol B (10) as the key intermediate.