99756-37-3

Basic information

• Product Name: 1,4-DIBENZOYL-2,3:5,6-DI-O-ISOPROPYLIDENE-MYO-INOSITOL
• Synonyms: 1,2:4,5-BIS-O-(1-METHYLETHYLIDENE)-MYO-INOSITOL DIBENZOATE;1,4-BZ2-IPRY2-INO;1,4-DIBENZOYL-2,3:5,6-DI-O-ISOPROPYLIDENE-MYO-INOSITOL
• CAS NO: 99756-37-3
• Molecular Formula: C₂₆H₂₈O₈
• Molecular Weight: 468.499
• Mol File: 99756-37-3.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,4-DIBENZOYL-2,3:5,6-DI-O-ISOPROPYLIDENE-MYO-INOSITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIBENZOYL-2,3:5,6-DI-O-ISOPROPYLIDENE-MYO-INOSITOL(99756-37-3)
• EPA Substance Registry System: 1,4-DIBENZOYL-2,3:5,6-DI-O-ISOPROPYLIDENE-MYO-INOSITOL(99756-37-3)

Safety Data

• Hazardous Substances Data: 99756-37-3(Hazardous Substances Data)

Usage

General Description

1,4-DIBENZOYL-2,3:5,6-DI-O-ISOPROPYLIDENE-MYO-INOSITOL, also known as DBI, is a synthetic compound with potential applications in the field of organic chemistry. It is a derivative of myo-inositol, a naturally occurring compound with various biological activities. DBI is widely used as a chiral auxiliary in organic synthesis, particularly in the preparation of optically pure compounds. It is also used as a starting material for the synthesis of other complex organic molecules, including pharmaceuticals and agrochemicals. DBI is known for its ability to facilitate asymmetric synthesis and is considered an important building block in the field of organic chemistry.

Upstream product

• 98-88-4 benzoyl chloride 
• 106-95-6 allyl bromide 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 87-89-8 D-myo-inositol 
• 77-76-9 2,2-dimethoxy-propane 
• 116-11-0 2-Methoxypropene 

Downstream Products

• 131146-87-7 (±)-1-O-allyl-4-O-benzyl-2,3:5,6-di-O-isopropylidene-myo-inositol 
• 111392-10-0 (+/-)-1,2:4,5-di-O-isopropylidene-3,6-di-O-p-methoxybenzyl-myo-inositol 
• 111392-25-7 (+/-)-1,2:4,5-di-O-isopropylidene-3-O-p-methoxybenzyl-myo-inositol 
• 58706-24-4 (±)-3-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 58706-24-4 (+/-)-6-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 161972-49-2 (-)-1L-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol 
• 161972-48-1 (+)-1D-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol 
• 93133-75-6 Inositol 1,3,4-triphosphate 
• 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 
• 114419-08-8 (+)-1L-2,5,6-tri-O-benzyl-myo-inositol 
• 114419-09-9 (-)-1L-2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-myo-inositol 
• 115072-68-9 racemic 1,4-di-O-allyl-myo-inositol 
• 2068-89-5 (+/-)-myo-inositol-1,3,4-trisphosphate 
• 93133-76-7 D-Inositol 1,3,4-triphosphate 

Relevant articles and documents

A Chiral Phosphoramidite Reagent for the Synthesis of Inositol Phosphates

There is a paucity of chiral phosphoramidite reagents or chiral catalysis methods for the synthesis of biologically relevant inositol phosphates. A new C2-symmetrical chiral phosphoramidite has been developed and successfully applied to the syn

(±)-1,2:5,6-Di-O-isopropylidene-myo-inositol and (±)-6-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol: A practical preparation of key intermediates for myo-inositol phosphates

A simple and practical synthetic procedure for the versatile intermediates, (±)-1,2:5,6-di-O-isopropylidene-myo-inositol and (±)-6-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol, is described.

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.