Stereocontrol in the addition of nucleophiles to an optically active aldehyde derived from L-serine, leading to a short-step synthesis of (2S,3S,4R)-phytosphingosine

✍ Scribed by Makoto Shimizu; Ichiro Wakioka; Tamotsu Fujisawa

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 258 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01340-3

✦ Synopsis

The diastereoselective addition of dithianide to a chiral aldehyde derived from L-serine followed by hydrolysis of the dithiane moiety and the addition of dodecylacetylide gave a diastereomerically pure aminotriol derivative which, upon hydrogenation and deprotection, afforded (2S,3S,4R)-phytosphingosine in good overall yield in enantiomerically pure form.