57029-87-5

Upstream product

• 6763-47-9 rac-1,2-O-cyclohexylidene-myo-inositol 
• 108-24-7 acetic anhydride 
• 801301-07-5 L-3,6-di-O-[(S)-O-acetylmandeloyl]-1,2-O-cyclohexylidene-myo-inositol 
• 87-89-8 D-myo-inositol 
• 108-94-1 cyclohexanone 
• 41545-19-1 (+)-1,2:5,6-di-O-cyclohexylidene-myo-inositol 
• 34361-60-9 1L-1,2:4,5-di-O-cyclohexylidene-myo-inositol 
• 57089-24-4 3,2:1,6-di-O-cyclohexylidene-sn-myoinositol 
• 933-40-4 cycloxexanone dimethyl ketal 

Downstream Products

• 162315-10-8 C₂₈H₃₈O₆Si 
• 157542-48-8 D-2,3-O-cyclohexylidene-1,4,5,6-tetra-O-(bisbenzyloxyphosphoryl)-myo-inositol 
• 28841-60-3 D-myo-inositol 1,4,5,6-tetrakisphosphate 
• 162315-13-1 C₃₄H₅₀O₉Si 
• 24558-77-8 3,4,5,6-tetra-O-benzyl inositol 
• 170900-81-9 3,4,5,6-tetra-O-benzyl-1-O-p-methoxybenzyl-D-myo-inositol 
• 57029-85-3 1,4,5,6-tetra-O-benzyl-2,3-O-cyclohexylidene-sn-myo-inositol 

Relevant academic research and scientific papers

ACETYLATED PRODRUGS FOR DELIVERY ACROSS THE BLOOD-BRAIN BARRIER

The present disclosure relates to pharmaceutical compositions including a compound derived from a parent compound having a hydroxyl or amino moiety, wherein the hydroxyl in the parent compound is presented as an ester in the compound or the amino in the parent compound is presented as an amide in the compound, and their use to prevent or treat neurological disease.

Yb(OTf)3-Catalyzed Desymmetrization of myo-Inositol 1,3,5-Orthoformate and Its Application in the Synthesis of Chiral Inositol Phosphates

A variety of inositol phosphates including myo-inositol 1,4,5-trisphosphate, which is a secondary messenger in transmembrane signaling, were selectively synthesized via Yb(OTf)3-catalyzed desymmetrization of myo-inositol 1,3,5-orthoformate using a proline-based chiral anhydride as an acylation precursor. The investigated catalytic system could regioselectively differentiate the enantiotopic hydroxy groups of myo-inositol 1,3,5-orthoformate in the presence of a chiral auxiliary. This key step to generate a suitably protected chiral myo-inositol derivatives is described here as a unified approach to access inositol phosphates.

Chemoselective alcoholysis/acetolysis of trans-ketals over cis-ketals and its application in the total synthesis of the cellular second messenger, d-myo-inositol-1,4,5-trisphosphate

The involvement of natural phosphoinositols in various cellular signalling processes and the use of synthetic inositol derivatives in catalysis, supramolecular chemistry, natural product synthesis etc. gave momentum to myo-inositol chemistry. The presence of six secondary hydroxyl groups necessitates efficient protection-deprotection strategies for the synthesis of inositol derivatives. An important strategy for the initial protection of myo-inositol is the di-ketalization, which gives a mixture of three diketals, each having both cis-fused and trans-fused ketals. It is important to have methodologies either to selectively hydrolyze one of the two ketals or to convert one of the two acid labile ketals to an orthogonal base labile protecting group. By exploiting the difference in strain between trans-ketals and cis-ketals, we developed two operationally simple, high yielding methodologies for the chemoselective hydrolysis/acetolysis of trans-ketals (both isopropylidene and cyclohexylidene) of inositols, leaving the cis-ketal undisturbed, using cheap and easily preparable H2SO 4-silica as the catalyst. Also, terminal ketal moieties of carbohydrates and acyclic polyols could be selectively hydrolyzed/acetolyzed leaving the internal ketals intact. The use of methanol as the solvent leads to chemoselective alcoholysis but the use of DCM and acetic anhydride leads to chemoselective acetolysis. Applying this methodology, a short synthesis of d-myo-inositol-1,4,5-trisphosphate has been achieved. The Royal Society of Chemistry.

A stannylene strategy for regioselective acylation and phosphorylation of 1,2-cyclohexylidene-myo-inositol. Its convenient resolution and phosphatidylinositol synthesis

The bis(dibutylstannylene) derivative of 1,2-cyclohexylidene-myo-inositol reacted with (S)-O-acetylmandeloyl chloride and diphosphate tetraesters to give 3,6-dimandelate and 3-phosphate, respectively. Using the stannylene methodology for the optical resol

Resolution of synthetically useful myo-inositol derivatives using the chiral auxiliary O-acetylmandelic acid

Efficient methods for the resolution of various myo-inositol derivatives have been developed using O-acetylmandelic acid (OAM) as the chiral auxiliary. Various methods of introduction of the chiral auxiliary have been compared. DCC mediated coupling betwe

Synthetic strategies based on phosphite chemistry for inositol phosphates and phospholipids

On the basis of the phosphite chemistry, new phosphorylation and glycosylation methodologies were developed. These methods were efficiently used for the syntheses of phosphatidylinositol 3,4,5-trisphosphate, and 2,6-di-O-mannopyranosylphosphatidylinositol.

Immunoassay for inositols

Antibodies raised against derivatives of inositol are used to assay for specific isomers of inositol in a sample by first converting any inositol present in the sample to the derivative that was used to raise the antibody and then conducting an immunoassay for the inositol derivative in a conventional manner.

Synthesis of myo-inositol 1,4,6-trisphosphate, an analogue of myo-inositol 1,4,5-trisphosphate

myo-Inositol 1,4,6-trisphosphate, in optically inactive and active forms, was prepared in order to compare its biological activity with that of myo- inositol 1,3,4,6-tetrakisphosphate which releases Ca2+ from an intracellular store. myo-Inositol 1,4,6-trisphosphate, in optically inactive and active forms, was prepared in order to compare its biological with that of myo-inositol 1,2,4,6-tetrakisphosphate which releases Ca 2+ from an intracellular store.

A chemoenzymatic synthesis of D-myo-inositol 1,4,5-trisphosphate

Enzyme-catalyzed esterification of racemic 2,3-O-cyclohexylidene-myo-inositol (DL-1) proceeded exclusively in 1,4-dioxane to give optically pure L-1-O-acetyl-2,3-O-cyclohexylidene-myo-inositol (L-2) and D-2,3-O-cyclohexylidene-myo-inositol (D-1).A new practical route has been developed for the synthesis of D-myo-inositol 1,4,5-trisphosphate starting from D-1 via selective acylation of the 6-hydroxyl group.