291527-75-8

Basic information

• Product Name: (2R)-3-[(hydroxy{[(1R,2R,3R,4R,5S,6R)-2,3,4,6-tetrahydroxy-5-(phosphonooxy)cyclohexyl]oxy}phosphoryl)oxy]propane-1,2-diyl dihexadecanoate
• Synonyms: (2R)-3-[(Hydroxy{[(1R,2R,3R,4R,5S,6R)-2,3,4,6-tetrahydroxy-5-(phosphonooxy)cyclohexyl]oxy}phosphoryl)oxy]propane-1,2-diyl dihexadecanoate; Hexadecanoic acid, (1R)-2-[[hydroxy[[(1R,2R,3R,4R,5S,6R)-2,3,4,6-tetrahydroxy-5-(phosphonooxy)cyclohexyl]oxy]phosphinyl]oxy]-1-[[(1-oxohexadecyl)oxy]methyl]ethyl ester
• CAS NO: 291527-75-8
• Molecular Formula: C₄₁H₈₀O₁₆P₂
• Molecular Weight: 891.0118
• Mol File: 291527-75-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 921.1°C at 760 mmHg
• Flash Point: 510.9°C
• Density: 1.21g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: (2R)-3-[(hydroxy{[(1R,2R,3R,4R,5S,6R)-2,3,4,6-tetrahydroxy-5-(phosphonooxy)cyclohexyl]oxy}phosphoryl)oxy]propane-1,2-diyl dihexadecanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-3-[(hydroxy{[(1R,2R,3R,4R,5S,6R)-2,3,4,6-tetrahydroxy-5-(phosphonooxy)cyclohexyl]oxy}phosphoryl)oxy]propane-1,2-diyl dihexadecanoate(291527-75-8)
• EPA Substance Registry System: (2R)-3-[(hydroxy{[(1R,2R,3R,4R,5S,6R)-2,3,4,6-tetrahydroxy-5-(phosphonooxy)cyclohexyl]oxy}phosphoryl)oxy]propane-1,2-diyl dihexadecanoate(291527-75-8)

Safety Data

• Hazardous Substances Data: 291527-75-8(Hazardous Substances Data)

Upstream product

• 496808-59-4 Hexadecanoic acid (R)-2-(diisopropylamino-methoxy-phosphanyloxy)-1-hexadecanoyloxymethyl-ethyl ester 
• 2857-97-8 trimethylsilyl bromide 
• 496922-03-3 1D-O-(1,2-dipalmitoyl-sn-glycerol-3-O-methylphospho)-2,3,4,6-O-tetrakis(methoxymethylene)-myo-inositol-5-(dibenzyl phosphate) 
• 165689-91-8 1D-O-(1,2-di-O-palmitoyl-sn-glycerol-3-O-methylphospho)-2,4,5,6-O-tetrakis(methoxymethylene)-myo-inositol 3-(dibenzyl phosphate) 

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 dipalmitoyl-phosphatidylinositol 5-phosphate and its modified biological tools

Synthesis of a dipalmitoyl analog of phosphatidylinositol 5-phosphate with the racemic inositol skeleton was achieved via a key intermediate, 1,2-cyclohexylidene-3,4-tetraisopropyldisiloxanyl-myo-inositol. Probes bearing a fluorophore, NBD on a fatty acid chain and a resin for affinity chromatography were also prepared due to biological interest in cell division. (C) 2000 Elsevier Science Ltd.

General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives

The D-3-phosphorylated wyo-inositol phospholipids PtdIns(3)P, PtdIns(3,4)P2, PtdIns(3,4,5)P3 and PtdIns(3,5)P2 were synthesised from /yo-inositol orthoformate 8. Key transformations included the regioselective DIBAL- and trimethylaluminium-mediated cleavages of wiyo-inositol orthoformate intermediates and a resolution-protection protocol using the camphor acetals 17. The final reductive debenzylation was effected with Pearlman's catalyst [Pd(OH)J in the presence of sodium hydrogen carbonate. The biological properties of the phospholipids were evaluated against various protein kinases (PKB and PDK-1) in which they played an important activation role.