An efficient synthesis of d-ribo- and l-lyxo-phytosphingosine from d-tartaric acid |
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Authors: | Xuequan Lu |
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Institution: | Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, NY 11367-1597, USA |
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Abstract: | The preparations of d-ribo- and l-lyxo-phytosphingosines (1, 2) are described. Chelation-controlled addition of tetradecylmagnesium bromide to pentylidene-protected d-threitol aldehyde 6 afforded the key intermediate tetrol 7, providing the desired l-lyxo stereochemistry of phytosphingosine. Inversion at C4 of intermediate 7 provided the d-ribo stereochemistry. |
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Keywords: | Sphingolipid Lipid synthesis Phytosphingosine |
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