168411-99-2

Basic information

• Product Name: 3-O-TERT-BUTYLDIMETHYLSILYL-D-ERYTHRO-SPHINGOSYLPHOSPHORYLCHOLINE
• Synonyms: 3-O-TERT-BUTYLDIMETHYLSILYL-D-ERYTHRO-SPHINGOSYLPHOSPHORYLCHOLINE
• CAS NO: 168411-99-2
• Molecular Formula: C29H63N2O5PSi
• Molecular Weight: 578.88
• Product Categories: Chemical Activators;Activators;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators
• Mol File: 168411-99-2.mol

Chemical Properties

• Appearance: /
• Solubility: Methanol
• CAS DataBase Reference: 3-O-TERT-BUTYLDIMETHYLSILYL-D-ERYTHRO-SPHINGOSYLPHOSPHORYLCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-TERT-BUTYLDIMETHYLSILYL-D-ERYTHRO-SPHINGOSYLPHOSPHORYLCHOLINE(168411-99-2)
• EPA Substance Registry System: 3-O-TERT-BUTYLDIMETHYLSILYL-D-ERYTHRO-SPHINGOSYLPHOSPHORYLCHOLINE(168411-99-2)

Safety Data

• Hazardous Substances Data: 168411-99-2(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

InChI:InChI=1/C29H63N2O5PSi/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-28(36-38(8,9)29(2,3)4)27(30)26-35-37(32,33)34-25-24-31(5,6)7/h22-23,27-28H,10-21,24-26,30H2,1-9H3/b23-22+/t27-,28+/m0/s1

Upstream product

• 1357001-19-4 C₃₄H₇₁N₂O₇PSi 

Downstream Products

• 1670-26-4 sphingosylphosphorylcholine 

Relevant articles and documents

NMR-based conformational analysis of sphingomyelin in bicelles

Sphingomyelin (SM) is a common sphingolipid in mammalian membranes and is known to be substantially involved in cellular events such as the formation of lipid rafts. Despite its biological significance, conformation of SM in a membrane environment remains

Efficient Synthesis of Sphingosine-1-phosphate, Ceramide-1-phosphate, Lysosphingomyelin, and Sphingomyelin

Readily available D-erythro-azidosphingosine is transformed into 3-O-silyl-protected derivative 6.Reduction of the azido group afforded 3-O-silyl-protected sphingosine 7 which was either converted into N-Fmoc-protected derivative 8 or via N-acylation into ceramide derivatives 16 and 17, respectively.Treatment of 6, 8, and 16 with bis(2-cyanoethoxy)(diisopropylamino)phosphane as monofunctional phsophitylating agent, subsequent oxidation and then removal of the protective groups furnished azidosphingosine-1-phosphate (11), sphingosine-1-phosphate (2), and ceramide-1-phosphate (4), respectively.Treatment of 8 and 17 with bis(diisopropylamino)(2-cyanoethoxy)phosphane as bifunctional phosphitylating agent and then with choline afforded after oxidation and subsequent deprotection lysosphingomyelin (3) and sphingomyelin (1), respectively in high overall yields.All final products are sterochemically pure and possess D-erythro configuration in the sphingosine moiety. - Key Words: Phosphosphingolipids, synthesis of/ Azidosphingosine/ Azidosphingosine-1-phosphate/ Phosphitylation/ Sphingosine phosphates