78739-31-8

Basic information

• Product Name: threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline
• Synonyms: threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline
• CAS NO: 78739-31-8
• Molecular Weight: 385.59
• Mol File: 78739-31-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline(CAS DataBase Reference)
• NIST Chemistry Reference: threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline(78739-31-8)
• EPA Substance Registry System: threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline(78739-31-8)

Safety Data

• Hazardous Substances Data: 78739-31-8(Hazardous Substances Data)

Upstream product

• 5333-86-8 ethyl benzimidate hydrochloride 
• 554-62-1 D-ribo-phytosphingosine 
• 572922-35-1 2-phenyl-4-(S)-[(1R,2R)-1,2-dihydroxyhexadecyl]-1,3-oxazoline 
• 825-60-5 benzimidic acid ethyl ester 
• 41765-25-7 C₂₃H₄₇Al 
• 78715-84-1 4-formyl-2-phenyl-Δ²-oxazoline 
• 765-13-9 pentadec-1-yne 
• 78715-83-0 methyl (S)-2-phenyl-4,5-dihydrooxazole-4-carboxylate 

Downstream Products

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 103931-07-3 Toluene-4-sulfonate(2-{[(E)-(2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyloxy]-methoxy-thiophosphoryloxy}-ethyl)-trimethyl-ammonium; 
• 115523-49-4 Toluene-4-sulfonate(2-{[(E)-(2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyloxy]-methoxy-phosphoryloxy}-ethyl)-trimethyl-ammonium; 
• 115523-47-2 Toluene-4-sulfonate(2-{[(E)-(2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyloxy]-methoxy-phosphanyloxy}-ethyl)-trimethyl-ammonium; 
• 103931-10-8 C₅₇H₁₀₁N₂O₅PSSi 
• 115523-51-8 C₅₇H₁₀₁N₂O₆PSi 
• 103931-05-1 Diisopropyl-phosphoramidous acid (E)-(2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyl ester methyl ester 
• 78779-93-8 N-oleoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer) 
• 78779-90-5 threo-1-O-benzoylceramide 
• 78715-91-0 threo-N-acetyl-1-O-benzoylsphingosine 
• 78779-94-9 N-oleoyl-1-O-β-D-galactosyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer) 
• 78779-92-7 N-oleoyl-1-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-D-sphingosine (threo epimer) 
• 143615-69-4 (2S,3S,4E)-2-N-acetylamino-1,3-dihydroxyoctadec-4-ene 
• 78779-96-1 N,O,O-triacetyl-L-threo-C₁₈-sphingosine 

Relevant articles and documents

A rapid and efficient synthesis of D-erythro-sphingosine from D-ribo-phytosphingosine

In this paper we describe the concise synthesis of D-erythro-sphingosine starting from the readily available chiral building block D-ribo- phytosphingosine. The title compound is the ubiquitous sphingolipid from which most mammalian ceramides are derived. Our work is based on the existing literature in which the same sphingoid base is used as a starting point and culminates in what we believe is the most efficient synthesis of D-erythro-sphingosine reported to date.

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.