An efficient synthesis of d-ribo-C18-phytosphingosine and l-arabino-C18-phytosphingosine from d-fructose
- Resource Type
- Article
- Authors
- Perali, Ramu Sridhar; Mandava, Suresh; Chalapala, Sudharani
- Source
- Tetrahedron. Dec2011, Vol. 67 Issue 48, p9283-9290. 8p.
- Subject
- *ORGANIC synthesis
*FRUCTOSE
*SPHINGOSINE
*CHEMICAL reduction
*STEREOCHEMISTRY
*HYDROGENATION
*HYDROPHOBIC surfaces
*METATHESIS reactions
- Language
- ISSN
- 0040-4020
Abstract: d-ribo-C18-phytosphingosine and l-arabino-C18-phytosphingosine were synthesised starting from commercially inexpensive d-fructose. Metal-mediated fragmentation and stereoselective reduction were used as key steps to provide the hydrophilic portion of d-ribo and l-arabino phytosphingosines. Grubbs’ cross-metathesis and hydrogenation allowed the incorporation of hydrophobic tail. [Copyright &y& Elsevier]