title: Protected sphingosine from phytosphingosine as an efficient acceptor in glycosylation reaction.
abstract: A convenient, simple, and high-yielding five-step synthesis of a sphingosine acceptor from phytosphingosine is reported, and its behavior in glycosylation reactions is described. Different synthetic paths to sphingosine acceptors using tetrachlorophthalimide as a protecting group for the sphingosine amino function and different glycosylation methods have been explored. Among the acceptors tested, the easiest accessible acceptor, unprotected on the two hydroxyl groups in positions 1 and 3, was regioselectively glycosylated on the primary position, the regioselectivity depending on the donor used.
authors.affiliation: Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale A. Avogadro , L.go Donegani, 2-28100 Novara, Italy.
authors.forename: Roberta
authors.initials: R
authors.lastname: Di Benedetto
authors.forename: Luca
authors.initials: L
authors.lastname: Zanetti
authors.forename: Monica
authors.initials: M
authors.lastname: Varese
authors.forename: Mehdi
authors.initials: M
authors.lastname: Rajabi
authors.forename: Riccardo
authors.initials: R
authors.lastname: Di Brisco
authors.forename: Luigi
authors.initials: L
authors.lastname: Panza
mesh_terms: D006031:Glycosylation; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C012491:phytosphingosine; D013110:Sphingosine