Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using a threitol acetal synthon.
The first synthesis of an isosteric phosphonate analogue of the aminotriol lipid phytosphingosine (3), together with an improved synthesis of (2S,3S,4S)-phytosphingosine (2), are described. A key intermediate is 3-pentylidene acetal 9, which was prepared in two steps from dimethyl 2,3-O-benzylidene-d-tartrate (7).
Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.
Xuequan
X
Lu
Hoe-Sup
HS
Byun
Robert
R
Bittman
D000080:Acetals / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D013110:Sphingosine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000737:chemistry
D000080:Acetals; D007202:Indicators and Reagents; D009943:Organophosphorus Compounds; D013402:Sugar Alcohols; C481930:lyxo-phytosphingosine; C003460:threitol; D013110:Sphingosine