title: A facile synthesis of D-ribo-C(20)-phytosphingosine and its C2 epimer from D-ribose.
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.
authors.affiliation: Department of Organic Chemistry, P.J. Šafárik University, Moyzesova, Košice, Slovak Republic. miroslava.martinkova@upjs.sk
authors.forename: Miroslava
authors.initials: M
authors.lastname: Martinková
authors.forename: Jozef
authors.initials: J
authors.lastname: Gonda
authors.forename: Kvetoslava
authors.initials: K
authors.lastname: Pomikalová
authors.forename: Jozef
authors.initials: J
authors.lastname: Kožíšek
authors.forename: Juraj
authors.initials: J
authors.lastname: Kuchár
mesh_terms: D015394:Molecular Structure; D012266:Ribose / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012266:Ribose; C012491:phytosphingosine; D013110:Sphingosine