13053-57-1

Basic information

• Product Name: N-HEXADECANOYL-D-SPHINGOSINE-1-PHOSPHOCHOLINE
• Synonyms: N-HEXADECANOYL-D-SPHINGOSINE-1-PHOSPHOCHOLINE;N-PALMITOYL-D-SPHINGOMYELIN
• CAS NO: 13053-57-1
• Molecular Formula: C39H79N2O6P
• Molecular Weight: 703.03
• Mol File: 13053-57-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: N-HEXADECANOYL-D-SPHINGOSINE-1-PHOSPHOCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-HEXADECANOYL-D-SPHINGOSINE-1-PHOSPHOCHOLINE(13053-57-1)
• EPA Substance Registry System: N-HEXADECANOYL-D-SPHINGOSINE-1-PHOSPHOCHOLINE(13053-57-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13053-57-1(Hazardous Substances Data)

Upstream product

• 127028-37-9 (2S,3R,4E)-2-hexadecanoylamino-1-phosphorylcholine-3-(tert-butyldimethylsilyloxy)-octadecene 
• 3163-37-9 (E)-hexadec-2-enal 
• 26993-32-8 (E)-hexadec-2-en-1-ol 
• 135251-95-5 (2E)-ethyl 2-hexadecenoate 
• 124-25-4 myristylaldehyde 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 4201-55-2 (2S,3R,4E)-3-benzoyl-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 100680-49-7 (2S,3R,4E)-3-benzoyl-1-(triphenylmethyl)-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 94198-71-7 (2S,3R,4E)-1-(triphenylmethyl)-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 4201-58-5 (2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 57-10-3 1-hexadecylcarboxylic acid 
• 860021-45-0 (4S)-4-[(1R)-1-(tert-butyldiphenylsilyloxy)-hexadec-2-enyl]-2-chloro-2-oxo-[1,3,2]-oxazaphospholidine 
• 55357-38-5 choline tosylate 
• 112-67-4 n-hexadecanoyl chloride 

Relevant articles and documents

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NOVEL SYNTHESIS INTERMEDIATES FOR OBTAINING DERIVATIVES OF SPHINGOSINES, CERAMIDES AND SPHINGOMYELINS WITH GOOD YIELDS

The subject matter of the present invention is the novel molecules of formulae E, E′ and F. These molecules prove to be synthesis intermediates that are very advantageous for the manufacture of derivatives of sphingosine or of ceramides functionalized in position 1, with good yields, in which R1 and R2 are fatty chains, R3 is an alkyl group and R4 is a protective group for alcohol functions. Another subject of the invention is the use of the intermediates of type F for converting same into intermediates of type G, by means of reduction in the presence of lithium borohydride. The G molecules are precursors that are known to make it possible to obtain sphingolipids or sphingomyelin.

METHODS FOR THE SYNTHESIS OF SPHINGOMYELINS AND DIHYDROSPHINGOMYELINS

The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.

SPHINGOMYELIN, INTERMEDIATES THEREOF AND METHODS FOR PREPARATION OF SAME

The invention concerns novel oxazaphospholanes, cyclic and acyclic, and to their use in the synthesis of sphingomyelin and sphingomyelin analogous as well as to synthetic sphingomyelins obtained therefrom. One group of oxazaphospholane according to the invention has the general formula (1) disclosed herein. Specifically, the invention provides the 2S, 3R stereoisomers of the disclosed oxazaphospholanes and sphingomyelins and synthetic methods for their preparation.