443793-76-8Relevant academic research and scientific papers
Synthesis of sphingomyelin carbon analogues as sphingomyelinase inhibitors
Hakogi, Toshikazu,Monden, Yoshiko,Taichi, Misako,Iwama, Seiji,Fujii, Shinobu,Ikeda, Kiyoshi,Katsumura, Shigeo
, p. 4839 - 4846 (2007/10/03)
The highly efficient and stereocontrolled syntheses of sphingomyelin carbon analogues 1 and 2 were achieved by effectively utilizing Hofmann rearrangement of enantiomerically pure β-hydroxyamide 7, which was prepared by an asymmetric hydrogenation of α-acyl-γ-butyrolactone 9 and ring opening with NH3. Intermediary isocyanate 6 was selectively trapped with the vicinal hydroxy group in an intramolecular fashion to produce an oxazolidinone derivative, 5. In the synthesis of a quite polar compound such as 1, a convenient one-pot procedure of the introduction of a benzyloxycarbonyl group into the hydroxy group resulting from the oxazolidinone ring opening is another key point, because, in addition to the efficiency, this protecting group was easily removable by a simple procedure and workup at the final step. Both synthesized compounds 1 and 2 showed moderate inhibitory activity toward sphingomyelinase from B. cereus.
