title: Efficient and selective synthesis of D-arabino-, D-lyxo-, and D-xylo-phytosphingosine from D-ribo-phytosphingosine.
abstract: A new high-yield approach to the regio- and stereoselective synthesis of d-arabino-, D-lyxo-, and D-xylo-phytosphingosines from inexpensive D-ribo-phytosphingosine is described. The synthetic methodologies mainly rely on the selective configurational inversion of the stereocenter through a neighboring group participation mechanism.
authors.affiliation: College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Nakyong
authors.initials: N
authors.lastname: Lee
authors.forename: Sukjin
authors.initials: S
authors.lastname: Lee
authors.forename: Taeho
authors.initials: T
authors.lastname: Lee
authors.forename: Yun Mi
authors.initials: YM
authors.lastname: Lee
mesh_terms: D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C012491:phytosphingosine; D013110:Sphingosine