A facile synthesis of d-ribo-C20-phytosphingosine and its C2 epimer from d-ribose |
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| Authors: | Miroslava Martinková ,Jozef Gonda,Kvetoslava Pomikalová ,Jozef Ko?í &scaron ek,Juraj Kuchá r |
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| Affiliation: | aInstitute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, Sk-040 01 Košice, Slovak Republic;bInstitute of Physical Chemistry and Chemical Physics, Department of Physical Chemistry, Slovak University of Technology, Radlinského 9, Sk-812 37 Bratislava, Slovak Republic;cInstitute of Chemical Sciences, Department of Inorganic Chemistry, P.J. Šafárik University, Moyzesova 11, Sk-040 01 Košice, Slovak Republic |
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| Abstract: | A facile synthetic route to d-ribo-C20-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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| Keywords: | Sphingolipids Phytosphingosine Overman rearrangement Trichloroacetamides |
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