title: Regioselective inversion of the hydroxyl group in D-ribo-phytosphingosine via a cyclic sulfate and bis-sulfonate intermediate.
abstract: The selective synthesis of D-xylo- and D-lyxo-phytosphingosines from commercially available D-ribo-phytosphingosine is described. Thermolysis of the N-carbonyl protected cyclic sulfate led to an inversion of configuration of the proximal hydroxyl group to give the xylo-isomer, whereas the corresponding bis-sulfonate resulted in an inversion of configuration of the distal hydroxyl group to give the lyxo-isomer. This study allowed the comparison between a cyclic sulfate and a bis-sulfonate in an intramolecular substitution reaction involving a carbonyl oxygen nucleophile.
authors.affiliation: College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea.
authors.forename: Yun Mi
authors.initials: YM
authors.lastname: Lee
authors.forename: Dong Jae
authors.initials: DJ
authors.lastname: Baek
authors.forename: Seokwoo
authors.initials: S
authors.lastname: Lee
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
mesh_terms: D000476:Alkanesulfonates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry*
chemical_list: D000476:Alkanesulfonates; C521790:D-ribo-phytosphingosine; D013431:Sulfates; C458140:xylo-phytosphingosine; D013110:Sphingosine