Synthesis of a versatile (S)-3-(hydroxymethyl)butane-1,2,4-triol building block and its application for the stereoselective synthesis of N-homoceramides.
[structures: see text] A versatile (S)-3-(hydroxymethyl)butane-1,2,4-triol building block has been synthesized starting from D-isoascorbic acid, a common food preservative. The key transformation in this approach was the introduction of branching through a high yield and fully regioselective epoxide opening. This flexible synthon has been elaborated to a new class of (dihydro-)N-homo(phyto)ceramides.
Hillaert
Ulrik
U
Laboratory for Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Ghent University, Harelbekestraat 72, B-9000 Ghent, Belgium.
Van Calenbergh
Serge
S
D001205:Ascorbic Acid / Q000737:chemistry*; D000440:Butanols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry; D005520:Food Preservatives / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism
C513048:(S)-3-(hydroxymethyl)butane-1,2,4-triol; D000440:Butanols; D002518:Ceramides; D005520:Food Preservatives; D007202:Indicators and Reagents; C005056:isoascorbic acid; D001205:Ascorbic Acid