536-14-1

Upstream product

• 75-50-3 trimethylamine 
• 875112-70-2 2-bromoethyl (2S)-N-(1-oxohexadecyl)amino-(3R)-hydroxy-(4E)-octadecenyl methyl phosphate 
• 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 
• 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 

Relevant academic research and scientific papers

An efficient route to N palmitoyl D crythro sphingomyelin and its 13C-labeled derivatives

We describe here a practical and efficient route to a homogeneous N palmitoyl D crythro sphingomyelin and its 13C-labeled derivatives. (2S, 3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-4-octadecene-l-ol1 was converted to the sphingosine equivalent 2 by treatment with triphenylphosphine and water. Amine 2 was then coupled with palmitic acid, affording the ceramide derivative 3a. In the following two reactions the phosphorylcholine functional group was generated by using 2-chloro-2-oxo-1,3,2-dioxaphospholane and trimethylamine, respectively. The final deprotection of the secondary hydroxyl group in 5a produced the desired N palmitoyl D crythro sphingomyelin 6a. The overall yield of this five-step synthesis is 43%. The melting point, 213-215°C, the specific rotation, [α]20D - +6.8 (c= 1-3, CH2Cl2MeOH 1:1) and 1H-and 13C-NMR data indicate that the synthetic sphingomyelin is enantiomerically pure. The 13C-labeled derivatives 6b, 6c and 6d were synthesized by employing the same scheme.

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.

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.

Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis

A highly efficient and versatile method for the synthesis of various sphingolipids, such as sphingomyelin, ceramide, sphingosine, sphingosine 1-phosphate, and functionalized sphingosine derivatives, was established by two types of combinations of the olefin cross metathesis reaction. One reaction was between the same olefin part and appropriate amino alcohols, which were prepared starting from N-Boc-L-serine, and the other was between appropriate olefins and the same amino alcohol.

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.

A useful synthesis of D-erythro-sphingomyelins

A practical and efficient synthesis of N-palmitoyl-D-erythro-sphongomyelin is reported here, providing a general method for the preparation of various sphingomyelins bearing different N-acyl chains.