An efficient synthesis of d-ribo-C18-phytosphingosine and l-arabino-C18-phytosphingosine from d-fructose

descriptionPublicationkeyboard_double_arrow_right Article 01 Dec 2011 English Publisher:Elsevier BVJournal:Tetrahedron, volume 67, pages 9,283-9,290 (issn: 0040-4020,

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Authors: Ramu Sridhar Perali; Suresh Mandava; Sudharani Chalapala;

doi: 10.1016/j.tet.2011.10.003

An efficient synthesis of d-ribo-C18-phytosphingosine and l-arabino-C18-phytosphingosine from d-fructose

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Abstract

Abstract d - ribo -C 18 -phytosphingosine and l - arabino -C 18 -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.

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University of Hyderabad
India

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