126624-40-6

Upstream product

• 1492-30-4 4-nitrophenyl palmitate 
• 126624-36-0 (2R)-(4E)-2-aminooctadec-4-ene-1-ol 
• 26993-32-8 (E)-hexadec-2-en-1-ol 
• 126624-35-9 (R,E)-N-(1-hydroxyoctadec-4-en-2-yl)acetamide 
• 66222-08-0 (E)-1-chloro-2-hexadecene 
• 2833-99-0 n-2-hexadecyn-1-ol 
• 765-09-3 1-bromotridecane 
• 204443-59-4 1-((R)-2-Azido-octadec-4-ynyloxy)-4-methoxy-benzene 
• 204443-56-1 4'-methoxyphenyl (S)-2-hydroxy-4-octadecynyl ether 
• 765-13-9 pentadec-1-yne 
• 204443-57-2 Hexadecanoic acid [(R)-1-(4-methoxy-phenoxymethyl)-heptadec-3-ynyl]-amide 
• 204443-58-3 Methanesulfonic acid (S)-1-(4-methoxy-phenoxymethyl)-heptadec-3-ynyl ester 

Relevant academic research and scientific papers

Enantioselective Synthesis of 3-Deoxy-(R)-sphingomyelin from (S)-1-(4′-Methoxyphenyl)glycerol

(R)-3-Deoxysphingomyelin (2) was prepared from (S)-1-(4′-methoxyphenyl)-glycerol (3). The latter was converted into either p-methoxyphenyl (PMP) (S)-oxiranylmethyl ether (5) or (R)-1-(4′-methoxyphenyl)glycerol 2,3-cyclic sulfate (6). Opening of 5 with lithium pentadecyne in the presence of BF3·Et2O gave PMP (S)-2-hydroxy-4-octadecynyl ether (7) in 65percent yield. Alternatively, opening of cyclic sulfate 6 with excess lithium pentadecyne in the presence of catalytic cuprous iodide, followed by acidic workup, gave 7 in 90percent yield. After introduction of the amide group via azide displacement, reduction, and N-acylation, simultaneous reduction of the triple bond and deprotection of the PMP group by Birch reduction (Li, EtNH2) provided 3-deoxy-N-palmitoyl-(A)-ceramide (9). Finally, phosphitylation of 9, oxidation of the cyclic phosphite with bromine, followed by in situ ring opening gave a (2-bromoethyl)phosphate ester, which on quaternization with aqueous trimethylamine afforded 3-deoxy-N-palmitoyl-(R)-sphingomyelin (2) in 49percent overall yield from PMP (S)-2-hydroxy-4-octadecynyl ether (7).