153265-90-8

Usage

Type

Synthetic chemical compound

Derivation

Derived from myo-inositol

Structure

A derivative of inositol with a butyryl group at position 1 and two benzoyl groups at positions 4 and 6

Usage

Commonly used as a reagent in organic chemistry reactions, particularly in the synthesis of inositol derivatives and other organic compounds

Application

Used as a building block for the creation of various pharmaceuticals and biologically active molecules

Industries

Potential applications in the food and cosmetic industries, as well as in medical research for its properties and functions in the human body.

InChI:InChI=1/C32H25NO4/c34-31(35)30(18-28-22-11-3-1-9-20(22)17-21-10-2-4-12-23(21)28)33-32(36)37-19-29-26-15-7-5-13-24(26)25-14-6-8-16-27(25)29/h1-17,29-30H,18-19H2,(H,33,36)(H,34,35)/t30-/m0/s1

Upstream product

• 98-88-4 benzoyl chloride 
• 98510-20-4 myo-Inositol orthoformate 
• 123-20-6 vinyl n-butyrate 
• 153325-42-9 4,6-di-O-benzoyl-myo-inositol 

Downstream Products

• 176589-78-9 1D-2-O-acetyl-1-O-butyryl-4,6-O-dibenzoyl-myo-inositol 
• 134932-19-7 (+)-1D-1,2,4,5,6-O-pentabenzoyl-myo-inositol 
• 176589-79-0 C₄₀H₄₀O₁₀ 
• 176589-80-3 Benzoic acid (1R,2S,3S,4R,5S,6R)-2,6-bis-benzyloxy-3,4,5-trihydroxy-cyclohexyl ester 
• 153265-91-9 C₂₇H₃₀O₉ 

Relevant academic research and scientific papers

Enzyme assisted synthesis of D-myo-inositol-1,2,6-trisphosphate

The title compound is prepared in enantiomerically pure form via a facile enzyme assisted route. Essential for the success of the described method were a) the highly enantioselective esterification of 4,6-O-dibenzoyl-myo-inositol 2, b) the selective acylation of the axial hydroxyl function in 3 and c) the selective, base catalysed methanolysis of one benzoate group in 5. The obtained, selectively protected 1,2,6-triol 6 was converted into the title compound 7 by phosphorylation using N,N-dimethyl dibenzyl phosphoamidite followed by deprotection.

Enzyme Assisted Synthesis of Enantiomerically Pure myo-Inositol Derivatives - Chiral Building Blocks for Inositol Polyphosphates

Using a short and facile synthetic protocol involving highly selective, regio- and enentioselective enzymatic esterifications as key reaction steps, readily available myo-inositol is converted into optically pure 1D-1-O-butyryl-4,6-O-dibenzoyl-myo-inositol (-) - 5, a selectively protected central intermediate for the preparation of numerous inositol phosphates.