A facile synthesis of D-ribo-C(20)-phytosphingosine and its C2 epimer from D-ribose
Miroslava Martinková1, Jozef Gonda, Kvetoslava Pomikalová
1Department of Organic Chemistry, P.J. Šafárik University, Moyzesova, Košice, Slovak Republic. miroslava.martinkova@upjs.sk
Abstract:
A facile synthetic route to d-ribo-C(20)-phytosphingosine 31 and its C2 epimer 32 is described. The Overman rearrangement of allylic trichloroacetimidates derived from the known ribose derivative 7 has been used as the key step. The subsequent functional group interconversions in rearranged products 14 and 15 followed by Wittig olefination, Pd/C-mediated reduction and the removal of protecting groups successfully constructed the final molecules.
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