58526-04-8

Basic information

• Product Name: 1D-1,4-di-O-benzyl-2,3-O-cyclohexylidene-myo-inositol
• Synonyms: 1D-1,4-di-O-benzyl-2,3-O-cyclohexylidene-myo-inositol
• CAS NO: 58526-04-8
• Molecular Weight: 440.536
• Mol File: 58526-04-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1D-1,4-di-O-benzyl-2,3-O-cyclohexylidene-myo-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: 1D-1,4-di-O-benzyl-2,3-O-cyclohexylidene-myo-inositol(58526-04-8)
• EPA Substance Registry System: 1D-1,4-di-O-benzyl-2,3-O-cyclohexylidene-myo-inositol(58526-04-8)

Safety Data

• Hazardous Substances Data: 58526-04-8(Hazardous Substances Data)

Upstream product

• 6763-47-9 rac-1,2-O-cyclohexylidene-myo-inositol 
• 34361-60-9 1,2:4,5-dicyclohexylidene-myo-inositol 
• 108-94-1 cyclohexanone 
• 100-44-7 benzyl chloride 
• 1122-84-5 1-ethoxycyclohexene 
• 23486-92-2 3,6-di-O-benzyl-1,2:4,5-di-O-cyclohexylidene-D(L)-myo-inositol 
• 34361-60-9 1L-1,2:4,5-di-O-cyclohexylidene-myo-inositol 
• 191488-22-9 1L-1-O-(L-O-acetylmandelyl)-3,6-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-myo-inositol 
• 23486-92-2 3,6-di-O-benzyl-1,2:4,5-di-O-cyclohexylidene-myo-inositol 
• 87-89-8 D-myo-inositol 
• 111331-54-5 DL-1,4-di-O-benzyl-2,3-O-cyclohexylidene-5,6-di-O-(p-methoxybenzyl)-myo-inositol 
• 111331-59-0 DL-1,4-Di-O-benzyl-5,6-bis-O-(4-methoxybenzyl)-myo-inositol 
• 35949-66-7 (+/-)-1,4-di-O-benzyl-2,3-O-cyclohexylidene-myo-inositol 
• 933-40-4 cycloxexanone dimethyl ketal 

Downstream Products

• 28140-40-1 1,4,5,6-tetra-O-benzyl-myo-inositol 
• 113084-86-9 1L-1,4-di-O-benzyl-2,3-O-cyclohexylidene-5,6-di-O-(p-methoxybenzyl)-myo-inositol 
• 57029-86-4 3,4,5,6-tetra-O-benzyl-1,2-O-cyclohexylidene-sn-myo-inositol 
• 57029-85-3 1,4,5,6-tetra-O-benzyl-2,3-O-cyclohexylidene-sn-myo-inositol 
• 24558-77-8 3,4,5,6-tetra-O-benzyl inositol 
• 115509-74-5 1⁽³⁾,2-O-cyclohexylidene-3⁽¹⁾,6⁽⁴⁾-di-O-benzyl-sn-myoinositol 
• 111331-59-0 DL-1,4-Di-O-benzyl-5,6-bis-O-(4-methoxybenzyl)-myo-inositol 
• 111465-38-4 D-3,6-di-O-benzyl-4,5-bis-O-(p-methoxybenzyl)-myo-inositol 
• 111331-59-0 1D-1,4-di-O-benzyl-5,6-di-O-(p-methoxybenzyl)-myo-inositol 
• 191488-22-9 1L-1-O-(L-O-acetylmandelyl)-3,6-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-myo-inositol 
• 191488-21-8 1D-1-O-(L-O-acetylmandelyl)-3,6-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-myo-inositol 
• 272775-91-4 1L-1-azido-3,6-di-O-benzyl-1-deoxy-myo-inositol 
• 330801-89-3 1L-2-O-acetyl-1-azido-3,6-di-O-benzyl-1-deoxy-myo-inositol 
• 330801-87-1 1L-1-azido-3,6-di-O-benzyl-1-deoxy-4,5-di-O-(p-methoxybenzyl)-scyllo-inositol 

Relevant articles and documents

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.

Total synthesis of spicamycin amino nucleoside.

[formula: see text] The first total synthesis of spicamycin amino nucleoside 2 has been achieved. The aminoheptose unit 5 was prepared stereoselectively from myo-inositol, and the characteristic N-glycoside linkage was constructed by way of Pd-catalyzed coupling reaction of 5 with 6-chloropurine derivative 6.

Synthesis and Some Properties of D-myo-Inositol 1,4,5-Tris(dihydrogen phosphate)

Optically active myo-inositol 1,4,5-tris(dihydrogen phosphate) 1, which has now been recognized as a second messenger in a new intracellular signal transduction system, has been prepared starting from myo-inositol.The key step, phosphorylation of an adequately protected polyhydroxy derivative, was accomplished by three methods, among which a phosphoramidite method using a new phosphitylating agent, o-xylylene N,N-diethylphosphoramidite, gave the triphosphoric ester in quantitative yield.Optical resolution was effectively realized by derivatization into diastereoisomeric l-menthoxyacetic esters.NMR spectra and optical rotation are shown to depend on the pH of an aqueous solution of compound 1.