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.

Key words

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

References

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4

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

16

Owing to the reported instability of 1, it was also characterized as the triacetate derivative 11.