An efficient synthesis of d-ribo- and l-lyxo-phytosphingosine from D-Tartaric acid (cas 147-71-7)

Add time:09/28/2019    Source:infona.pl

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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