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

摘要

The practical and efficient synthesis of D-erythro-sphm-gosine 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 is-allylic alcohol of sphingosine via a cyclic sulfate intermediate that contains a non-nucleophilic trifluoroacetamide protecting group.Sphingolipids are a structurally diverse class of lipids that contain long-chain aliphatic amino alcohols. They are important structural components of the plasma membranes of essentially all eukaryotic cells and play critical roles in many biological processes.1 Growing interest in the biological functions of sphingolipids has generated a desire to develop efficient methods for their synthesis. One of the important factors for the successful synthesis of natural and non-natural sphingolipids is the acquisition of the appropriate sphingoid bases, which are the principal backbone of sphingolipids.