120595-85-9

Basic information

• Product Name: Hexadecanoic acid, (1R)-1-bis(1-methylethyl)amino(phenylmethoxy)phosphinooxymethyl-1,2-ethanediyl ester
• Synonyms: Hexadecanoic acid, (1R)-1-bis(1-methylethyl)amino(phenylmethoxy)phosphinooxymethyl-1,2-ethanediyl ester
• CAS NO: 120595-85-9
• Molecular Formula: C₄₈H₈₈NO₆P
• Molecular Weight: 806.19
• Mol File: 120595-85-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Hexadecanoic acid, (1R)-1-bis(1-methylethyl)amino(phenylmethoxy)phosphinooxymethyl-1,2-ethanediyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Hexadecanoic acid, (1R)-1-bis(1-methylethyl)amino(phenylmethoxy)phosphinooxymethyl-1,2-ethanediyl ester(120595-85-9)
• EPA Substance Registry System: Hexadecanoic acid, (1R)-1-bis(1-methylethyl)amino(phenylmethoxy)phosphinooxymethyl-1,2-ethanediyl ester(120595-85-9)

Safety Data

• Hazardous Substances Data: 120595-85-9(Hazardous Substances Data)

Upstream product

• 6076-30-8 1,2-di-O-palmitoyl-sn-glycerol 
• 108549-21-9 benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite 
• 30334-71-5 1,2-dipalmitoyl-sn-glycerol 
• 183430-01-5 (+)-3-O-(4-methoxybenzyl)-1,2-di-O-hexadecanoyl-sn-glycerol 
• 30403-51-1 1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol 
• 57-10-3 1-hexadecylcarboxylic acid 
• 921-26-6 N,N-diisopropylphosphoramide dichloride 
• 56183-63-2 bis(diisopropylamino)chlorophosphine 
• 100-51-6 benzyl alcohol 
• 93696-28-7 bis(N,N-diisopropylamino)chlorophosphine 
• 1042289-75-7 rac-1,2-dipalmitoylglycerol 
• 128753-68-4 (benzyloxy)chloro(diisopropylamino)phosphane 

Downstream Products

• 1196677-69-6 3,4,5,6-tetra-O-benzyl-1-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-[((R)-2,3-dipalmitoyloxypropyl)-(benzyl)phosphoryl]-D-myo-inositol 
• 127996-98-9 dipalmitoyl PtdIns₄P 
• 869110-65-6 Hexadecanoic acid (R)-2-(benzyloxy-{4-[(S)-2,3-bis-(bis-tert-butoxycarbonylmethyl-amino)-propyl]-phenoxy}-phosphanyloxy)-1-hexadecanoyloxymethyl-ethyl ester 

Relevant articles and documents

Development of isotope-enriched phosphatidylinositol-4- And 5-phosphate cellular mass spectrometry probes

Synthetic phosphatidylinositol phosphate (PtdInsPn) derivatives play a pivotal role in broadening our understanding of PtdInsPnmetabolism. However, the development of such tools is reliant on efficient enantioselective and regioselective synthetic strategies. Here we report the development of a divergent synthetic route applicable to the synthesis of deuterated PtdIns4Pand PtdIns5Pderivatives. The synthetic strategy developed involves a key enzymatic desymmetrisation step using Lipozyme TL-IM. In addition, we optimised the large-scale synthesis of deuteratedmyo-inositol, allowing for the preparation of a series of saturated and unsaturated deuterated PtdIns4Pand PtdIns5Pderivatives. Experiments in MCF7 cells demonstrated that these deuterated probes enable quantification of the corresponding endogenous phospholipids in a cellular setting. Overall, these deuterated probes will be powerful tools to help improve our understanding of the role played by PtdInsPnin physiology and disease.

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.

SYNTHETIC MOLECULES HAVING IMMUNE ACTIVITY

The present invention is directed to synthetic molecules having biological activity similar to PIM (acyl glycerol phosphatidylinositol manno-oligosaccharide) activity, for use in the treatment and prevention of inflammatory or immune cell mediated diseases or disorders.