78715-85-2

Basic information

• Product Name: erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline
• Synonyms: erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline
• CAS NO: 78715-85-2
• Molecular Weight: 385.59
• Mol File: 78715-85-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline(CAS DataBase Reference)
• NIST Chemistry Reference: erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline(78715-85-2)
• EPA Substance Registry System: erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline(78715-85-2)

Safety Data

• Hazardous Substances Data: 78715-85-2(Hazardous Substances Data)

Upstream product

• 78715-83-0 methyl (S)-2-phenyl-4,5-dihydrooxazole-4-carboxylate 
• 825-60-5 benzimidic acid ethyl ester 
• 15890-72-9 laurylmagnesium bromide 
• 173531-24-3 (4S,1'S,2'R)-4-(1',2'-Epoxybut-3'-enyl)-2-phenyl-4,5-dihydrooxazole 
• 41765-25-7 C₂₃H₄₇Al 
• 78715-84-1 4-formyl-2-phenyl-Δ²-oxazoline 
• 765-13-9 pentadec-1-yne 
• 173531-22-1 Methanesulfonic acid (1R,2S,3R)-2,4-dihydroxy-3-methanesulfonyloxy-1-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-butyl ester 
• 173531-23-2 (1'R,2'R,4S)-1'-Methylsulfonyloxy-1'-(2-phenyl-4,5-dihydrooxazol-4-yl)but-3'-en-2'-ol 

Downstream Products

• 103931-07-3 Toluene-4-sulfonate(2-{[(E)-(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyloxy]-methoxy-thiophosphoryloxy}-ethyl)-trimethyl-ammonium; 
• 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; 
• 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; 
• 103931-10-8 C₅₇H₁₀₁N₂O₅PSSi 
• 115523-50-7 C₅₇H₁₀₁N₂O₆PSi 
• 104012-20-6 Diisopropyl-phosphoramidous acid (E)-(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyl ester methyl ester 
• 58909-84-5 sphingomyelin 
• 54336-64-0 (2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol 
• 78715-88-5 N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (erythro epimer) 
• 78715-86-3 erythro-1-O-benzoylceramide 
• 78715-90-9 erythro-N-acetyl-1-O-benzoylsphingosine 
• 5966-28-9 N-oleoyl-D-sphingosine (erythro form) 
• 78715-87-4 N-oleoyl-1-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (erythro form) 
• 2482-37-3 (2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene 

Relevant articles and documents

Efficient stereocontrolled synthesis of D-erythro-sphingosine from N-benzoyl-D-glucosamine

D-erythro-Sphingosine is synthesized from N-benzoyl-D-glucosamine 2 in a highly regio- and stereo-controlled manner. The key features in the synthesis involve the efficient conversion of compound 2 into the vinyl epoxide 10 and the subsequent SN2′-type reaction with a Grignard reagent in the presence of CuCN to afford the 1-O,2-N-protected sphingosine 11.

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.