876310-82-6

Basic information

• Product Name: (Z)-Octadec-9-enoic acid (R)-2-[{(1S,2S,3R,4S,5R,6R)-3-[bis-(2-cyano-ethoxy)-thiophosphoryloxy]-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy}-(2-cyano-ethoxy)-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester
• Synonyms: (Z)-Octadec-9-enoic acid (R)-2-[{(1S,2S,3R,4S,5R,6R)-3-[bis-(2-cyano-ethoxy)-thiophosphoryloxy]-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy}-(2-cyano-ethoxy)-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester
• CAS NO: 876310-82-6
• Molecular Weight: 1294.57
• Mol File: 876310-82-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-Octadec-9-enoic acid (R)-2-[{(1S,2S,3R,4S,5R,6R)-3-[bis-(2-cyano-ethoxy)-thiophosphoryloxy]-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy}-(2-cyano-ethoxy)-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-Octadec-9-enoic acid (R)-2-[{(1S,2S,3R,4S,5R,6R)-3-[bis-(2-cyano-ethoxy)-thiophosphoryloxy]-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy}-(2-cyano-ethoxy)-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester(876310-82-6)
• EPA Substance Registry System: (Z)-Octadec-9-enoic acid (R)-2-[{(1S,2S,3R,4S,5R,6R)-3-[bis-(2-cyano-ethoxy)-thiophosphoryloxy]-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy}-(2-cyano-ethoxy)-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester(876310-82-6)

Safety Data

• Hazardous Substances Data: 876310-82-6(Hazardous Substances Data)

Upstream product

• 24529-88-2 1,2-dioleoyl-sn-glycerol 

Relevant articles and documents

Chemical synthesis and molecular recognition of phosphatase-resistant analogues of phosphatidylinositol-3-phosphate

The remodeling of phosphatidylinositol polyphosphates in cellular membranes by phosphatases and kinases orchestrates the signaling by these lipids in space and time. To provide chemical tools to study the changes in cell physiology mediated by these lipids, three new metabolically stabilized (ms) analogues of phosphatidylinositol-3-phosphate (Ptdlns(3)P) were synthesized. We describe herein the total asymmetric synthesis of 3-methylphosphonate, 3-(monofluoromethyl)phosphonate and 3-phosphorothioate analogues of Ptdlns(3)P. From differentially protected D-myo-inositol key intermediates, a versatile phosphoramidite reagent was employed in the synthesis of Ptdlns(3)P analogues with diacylglyceryl moieties containing dioleoyl, dipalmitoyl, and dibutyryl chains. In addition, we introduce a new phosphorylation reagent, (monofluoromethyl)phosphonyl chloride, which has general applications for the preparation of "pKa-matched" monofluorophosphonates. These ms-Ptdlns(3)P analogues exhibited reduced binding activities with 15N-labeled FYVE and PX domains, as significant 1H and 15N chemical shift changes in the FYVE domain were induced by titrating ms-Ptdlns(3)P analogues into membrane-mimetic dodecylphosphocholine micelles. In addition, the Ptdlns(3)P analogues with dioleoyl and dipalmitoyl chains were substrates for the 5-kinase enzyme PIKfyve; the corresponding phosphorylated ms-PI(3,5)P2 products were detected by radio-TLC analysis.