A Practical and Cost-Effective Synthesis of d-erythro-Sphingosine from d-ribo-Phytosphingosine via a Cyclic Sulfate Intermediate

Abstract

The practical and efficient synthesis of d-erythro-sphingosine from commercially available d-ribo-phytosphingosine is described­. An important feature of this synthesis is the selective transformation of the 3,4-vicinal diol of phytosphingosine into the characteristic E-allylic alcohol of sphingosine via a cyclic sulfate intermediate that contains a non-nucleophilic trifluoroacetamide protecting group.

cyclic sulfates - protecting groups - reactive intermediates - sphingolipids - synthetic methods

References

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Phytosphingosine from fermentation can be purchased at low cost direct from suppliers such as Cosmoferm B. V. and Doosan Biotech BU.

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