180794-84-7

Basic information

• Product Name: D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-bis(phenylmethyl) phosphate
• Synonyms: D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-bis(phenylmethyl) phosphate
• CAS NO: 180794-84-7
• Molecular Formula: C₄₈H₄₉O₉P
• Molecular Weight: 800.87
• Mol File: 180794-84-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 858.4±65.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• PKA: 12.70±0.70(Predicted)
• CAS DataBase Reference: D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-bis(phenylmethyl) phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-bis(phenylmethyl) phosphate(180794-84-7)
• EPA Substance Registry System: D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-bis(phenylmethyl) phosphate(180794-84-7)

Safety Data

• Hazardous Substances Data: 180794-84-7(Hazardous Substances Data)

Upstream product

• 180794-83-6 (-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol 3-(dibenzyl phosphate) 
• 41545-19-1 (+)-1,2:5,6-di-O-cyclohexylidene-myo-inositol 
• 140887-09-8 (1R,2R,3S,4R,5R,6R)-2,3,4,6-Tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexanol 
• 141040-63-3 2,4,5,6-tetra-O-benzyl-DL-myo-inositol 
• 100-39-0 benzyl bromide 
• 129952-31-4 (+/-)-2,4,6-tri-O-benzyl-1,3-O-methylidene-D-myo-inositol 
• 129952-33-6 (1R,5S,6R,7S,8S,9S)-6,7,8,9-tetrakis(benzyloxy)-2,4-dioxabicyclo<3.3.1>nonane 
• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 180979-76-4 (+)-4,5,6-tri-O-benzyl-2,3-O-cyclohexylidene-1-O-(p-methoxybenzyl)-myo-inositol 
• 180979-78-6 (-)-3-O-allyl-4,5,6-tri-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol 
• 180794-80-3 (-)-6-O-benzyl-2,3:4,5-di-O-cyclohexylidene-1-O-(p-methoxybenzyl)-myo-inositol 
• 180979-77-5 (+)-4,5,6-tri-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol 
• 180794-81-4 (+)-6-O-benzyl-2,3-O-cyclohexylidene-1-O-(p-methoxybenzyl)-myo-inositol 
• 180794-82-5 (+)-3-O-allyl-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol 

Downstream Products

• 1188371-78-9 C₆₉H₇₅NO₁₄P₂ 

Relevant articles and documents

Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes

The synthesis of the complete family of phosphatidylinositol phosphate analogues (PIPs) from five key core intermediates A-E is described. These core compounds were obtained from myo-inositol orthoformate 1 via regioselective DIBAL-H and trimethylaluminium-mediated cleavages and a resolution-protection process using camphor acetals 10. Coupling of cores A-E with phosphoramidites 34 and 38, derived from the requisite protected lipid side chains, afforded the fully-protected PIPs. Removal of the remaining protecting groups was achieved via hydrogenolysis using palladium black or palladium hydroxide on carbon in the presence of sodium bicarbonate to afford the complete family of dipalmitoyl- and amino-PIP analogues 42, 45, 50, 51, 58, 59, 67, 68, 76, 77, 82, 83, 92, 93, 99 and 100. Investigations using affinity probes incorporating these compounds have identified novel proteins involved in the PI3K intracellular signalling network and have allowed a comprehensive proteomic analysis of phosphoinositide interacting proteins. The Royal Society of Chemistry 2010.

Synthesis of the D-3 series of phosphatidylinositol phosphates

The 3-mono-, 3,4-bis-, and 3,4,5-trisphosphates of L-α-phosphatidyl-D-myo-inositol have been synthesized in their optically active forms from the two enantiomers of 1,2:5,6-di-O-cyclohexylidene-myo-inositol. These chiral precursors were prepared by a facile biocatalytic resolution, in which the 4-butyryl ester of the racemic compound was subjected to enantioselective hydrolysis by porcine pancreatic lipase in a biphasic system. The overall yield from individual chiral precursors ranged from 32% for the 3,4,5-trisphosphate to 39% for the monophosphate.