58909-84-5

Basic information

• Product Name: N-STEAROYL-D-SPHINGOMYELIN
• Synonyms: N-STEAROYL-D-SPHINGOMYELIN;2,3-(N-steroylsphingosyl)-1-phosphocholine;N-Octadecanoyl-D-sphingosine-1-phosphocholine;N-Stearoyl-D-sphingomyelin semisynthetic;N-stearoyl-D-erythro-sphingosylphosphorylcholine;18:0 SM (d18:1/18:0)
• CAS NO: 58909-84-5
• Molecular Formula: C₄₁H₈₃N₂O₆P
• Molecular Weight: 731.089
• Mol File: 58909-84-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: N-STEAROYL-D-SPHINGOMYELIN(CAS DataBase Reference)
• NIST Chemistry Reference: N-STEAROYL-D-SPHINGOMYELIN(58909-84-5)
• EPA Substance Registry System: N-STEAROYL-D-SPHINGOMYELIN(58909-84-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 58909-84-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40+/m0/s1

Upstream product

• 75-50-3 trimethylamine 
• 115523-50-7 C₅₇H₁₀₁N₂O₆PSi 
• 127028-38-0 <(2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)-4-octadecene-1-yl> <2-(trimethylammonio)ethyl> phosphate 
• 114299-64-8 (2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol 
• 137905-29-4 (2S,3R,4E)-2-amino-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-ol 
• 168412-00-8 (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)-4-octadecene-1-ol 
• 153996-46-4 Diisopropyl-phosphoramidous acid (E)-(2S,3R)-3-(tert-butyl-dimethyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyl ester 2-cyano-ethyl ester 
• 104012-20-6 Diisopropyl-phosphoramidous acid (E)-(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyl ester methyl ester 
• 115523-49-4 Toluene-4-sulfonate(2-{[(E)-(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyloxy]-methoxy-phosphoryloxy}-ethyl)-trimethyl-ammonium; 
• 103931-03-9 (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol 
• 14617-86-8 4-nitrophenyl stearate 
• 41765-25-7 C₂₃H₄₇Al 
• 78715-85-2 erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline 
• 115523-47-2 Toluene-4-sulfonate(2-{[(E)-(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyloxy]-methoxy-phosphanyloxy}-ethyl)-trimethyl-ammonium; 

Downstream Products

• 54336-64-0 (2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol 

Relevant articles and documents

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

Synthesis of D-erythro-sphingomyelin and of D-erythro-ceramide-1-phosphoinositol

3-O-Silyl-protected azidosphingosine 3, readily available from D-erythro-azidosphingosine, is transformed into ceramidyl phosphite derivative 5 which is a versatile building block for the synthesis of ceramide-1-O-phosphate and derivatives. This is exhibited for the synthesis of the title compounds 1 and 2.

Synthesis and Spectral Properties of Chemically and Stereochemically Homogeneous Sphingomyelin and its Analogues

2-N-Stearoylspingosyl-1-phosphocholines of D-erythro (2S,3R) and L-threo (2S,3S) configurations and their phosphorothioyl analogues were obtained by a purely synthetic approarch using O-methyl-N,N-di-isopropylaminophosphorochloridite as the phosphitylating reagent for the formation of the phophodiester linkage.Final products were obtained pure in yields of 70-75 percent.The structure and the purity of synthesized compounds was determined using 1H, 13C, and 31P n.m.r. spectroscopy.With respect to the structure of the sphingosine long-chain base the synthetic D-erythro-SPM was found to be identical with the natural sphigomyelin from bovine brain whereas the semisynthetic N-palmitoylshingomyelin obtained via a deacylation-reacylation pathway comprises a mixture of D-erythro- and L-thero-SPM.The phosphorothioyl analogues of sphingomyelin synthesized by addition of elementar sulphur to intermediate phosphite were separated into individual diastereomers having opposite configuration at phosphorus.The absolute configurations of diastereomers at phosphorus were assigned based on the known stereospecifity of phospholipase C in the hydrolysis of phosphorothioyl analogues of phospholipids.1H N.m.r. data of synthesized compounds suggest that the configuration at C-3 of the sphingosine influences the average conformation of sphingomyelin with respect to the angle of rotation about the C(1)-C(2) bond.

The Synthesis and Absolute Configuration of Thiosphingomyelins

Four diastereoisomers of a thiophosphoryl analogue of sphingomyelin were synthesized by a general method employing phosphoroamidites and the absolute configurations of (+)-erythro-thiosphingomyelins at phosphorus were determined by stereospecific hydrolysis in the presence of phospholipases C.