Efficient Synthesis of d-erythro-Sphingosine and d-erythro-Azidosphingosine from d-ribo-Phytosphingosine via a Cyclic Sulfate Intermediate

Efficient Synthesis of d-erythro-Sphingosine and d-erythro-Azidosphingosine from d-ribo-Phytosphingosine via a Cyclic Sulfate Intermediate

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 t...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2006-10, Vol.71 (22), p.8661-8664
Hauptverfasser: KIM, Sanghee, LEE, Sukjin, LEE, Taeho, KO, Hyojin, KIM, Deukjoon
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Cyclization
Exact sciences and technology
Lipids
Molecular Structure
Organic chemistry
Preparations and properties
Sphingosine - analogs & derivatives
Sphingosine - chemical synthesis
Sphingosine - chemistry
Sulfates - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0614543