An efficient route to N-palmitoyl-d-erythro-sphingomyelin and its 13C-labeled derivatives

✍ Scribed by Zhengxin Dong; Jared A. Butcher Jr.

• Book ID: 103042313
• Publisher: Elsevier Science
• Year: 1993
• Tongue: English
• Weight: 432 KB
• Volume: 66
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(93)90029-3

✦ Synopsis

We describe here a practical and efficient route to a homogeneous N-palmitoyl-D-erythro-sphingomyelin and its 13C-labeled derivatives. (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-4-octadecene-l-ol 1 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-l,3,2-dioxaphospholane and trimethylamine, respectively. The final deprotection of the secondary hydroxyl group in 5a produced the desired N-palmitoyl-D-erythro-sphingomyelin 6a. The overall yield of this five-step synthesis is 43%. The melting point, 213-215°C, the specific rotation, [C~]20D=+6.8 (C= 1.3, CH2CI2/MeOH 1:1) and IH-and 13C-NMR data indicate that the synthetic sphingomyelin is enantiomerically pure. The 13C-labeled derivatives 6b, 6¢ and 6d were synthesized by employing the same scheme.