Tetrahedron

An efficient synthesis of d-ribo-C 18-phytosphingosine and l-arabino-C 18-phytosphingosine from d-fructose

RS Perali, S Mandava, S Chalapala

Index: Perali, Ramu Sridhar; Mandava, Suresh; Chalapala, Sudharani Tetrahedron, 2011 ,  vol. 67,  # 48  p. 9283 - 9290

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Citation Number: 12

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.