Novel, short, stereospecific synthesis of lyxo-(2R,3R,4R)-phytosphingosine and erythro-(2R,3S)-sphingosine.
Lyxo-phytosphingosine and erythro-sphingosine have been elaborated from a common intermediate. The key step in the reaction sequence involves stereo- and regiospecific functionalization of an olefin by intramolecular nucleophilic sulfinyl group participation.
Raghavan
Sadagopan
S
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India. purush101@yahoo.com
Rajender
A
A
D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007202:Indicators and Reagents; C481931:erythro-(2R,3S)-sphingosine; C481930:lyxo-phytosphingosine; D013110:Sphingosine