78715-84-1

Basic information

• Product Name: 4-Oxazolecarboxaldehyde, 4,5-dihydro-2-phenyl-, (S)-
• CAS NO: 78715-84-1
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Mol File: 78715-84-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-Oxazolecarboxaldehyde, 4,5-dihydro-2-phenyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Oxazolecarboxaldehyde, 4,5-dihydro-2-phenyl-, (S)-(78715-84-1)
• EPA Substance Registry System: 4-Oxazolecarboxaldehyde, 4,5-dihydro-2-phenyl-, (S)-(78715-84-1)

Safety Data

• Hazardous Substances Data: 78715-84-1(Hazardous Substances Data)

Upstream product

• 78715-83-0 methyl (S)-2-phenyl-4,5-dihydrooxazole-4-carboxylate 
• 825-60-5 benzimidic acid ethyl ester 

Downstream Products

• 126960-10-9 (4S,1'R,2'E)-4,5-Dihydro-4-(1'-hydroxy-2'-tetradecenyl)-2-phenyl-1,3-oxazole 
• 126960-11-0 (4S,1'S,2'E)-4,5-Dihydro-4-(1'-hydroxy-2'-tetradecenyl)-2-phenyl-1,3-oxazole 
• 78715-85-2 erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline 
• 78739-31-8 threo-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline 
• 100924-01-4 (2'E,6'E,4S,1'R)-4-(1'-hydroxy-7'-methyl-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazolin-2-ene 
• 100924-02-5 (2'E,6'E,4R,1'S)-4-(1'-hydroxy-7'-methyl-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazolin-2-ene 
• 115018-42-3 (4S,1'R,2'E,6'E)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole 
• 115018-43-4 (4S,1'S,2'E,6'E)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole 
• 115018-52-5 (4S,1'R,2'E,6'Z)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole 
• 115018-53-6 (4S,1'S,2'E,6'Z)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole 
• 350592-77-7 (S,R)-4-hydroxy-4-(4,5-dihydro-2-phenyl-4-oxazolyl)-1-butene 
• 350592-76-6 (S,S)-4-hydroxy-4-(4,5-dihydro-2-phenyl-4-oxazolyl)-1-butene 
• 350592-80-2 (S,S)-4-hydroxy-4-(4,5-dihydro-2-phenyl-4-oxazolyl)-1-butene acetate 
• 350592-85-7 (S,R)-4-hydroxy-4-(4,5-dihydro-2-phenyl-4-oxazolyl)-1-butene acetate 

Relevant articles and documents

Enantioselective synthesis of Aza sugars from amino acids. 2. The 3-hydroxy-2-hydroxymethylpyrrolidines

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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.

Useful Syntheses of erythro- and threo-N-Oleoyl-D-sphingosines (Ceramides) and Galactosylceramides (Cerebrosides) from L-Serine

The 4-(carbomethoxy)-2-phenyl-Δ2-oxazoline formed from L-serine provides the basis for a useful synthesis of ceramides and cerebrosides.The natural erythro configuration and its threo epimer are formed in equal amounts but are readily separated chromatographically, so that both epimers are available for experiments in which the properties of erythro and threo configurations are to be compared.The method produces the final cerebroside product on a scale of 100 mg or more.The optical purity of the product was shown to be close to 100percent.In addition to the threo epimer, other analogues of the natural cerebrosides with different chain le ngths and stereochemistries should be readily available by using the route developed.Such molecules are of interest to us for (13)C NMR and related studies of membrane organization.