title: Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate.
abstract: The synthesis of naturally occurring d-erythro-sphingosine and synthetically useful D-erythro-2-azidosphingosine from commercially available d-ribo-phytosphingosine is described. An important feature of this synthesis is the selective transformation of the 3,4-vicinal diol of phytosphingosine into the characteristic E-allylic alcohol of sphingosine via a cyclic sulfate intermediate.
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: Sukjin
authors.initials: S
authors.lastname: Lee
authors.forename: Taeho
authors.initials: T
authors.lastname: Lee
authors.forename: Hyojin
authors.initials: H
authors.lastname: Ko
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
mesh_terms: D003500:Cyclization; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013431:Sulfates / Q000737:chemistry*
chemical_list: C521789:D-erythro-azidosphingosine; C521790:D-ribo-phytosphingosine; D013431:Sulfates; D013110:Sphingosine