A simple and low cost synthesis of D-ERYTHRO-SPHINGOSINE (cas 123-78-4) and d-erythro-azidosphingosine from d-ribo-phytosphingosine: glycosphingolipid precursors

Add time:09/27/2019    Source:sciencedirect.com

D-ERYTHRO-SPHINGOSINE (cas 123-78-4) (1) and d-erythro-2-azidosphingosine (2) are both prepared from commercially available and cheap d-ribo-phytosphingosine (3) in a yield of 58% and 70%, respectively. A key transformation in the synthesis of d-erythro-sphingosine (1) is the palladium catalyzed regiospecific reduction of the Z-enol triflate 9. A crucial step in the synthesis of azidosphingosine 2 comprises a regio- and stereoselective in situ trans-elimination of the 4-O-triflate of azidophytosphingosine 13.

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