A rapid synthesis of sphingosine from phytosphingosine

Arumugam Sankar; I-Cheng Chen; Shun-Yuan Luo

doi:10.1016/j.carres.2018.04.006

A rapid synthesis of sphingosine from phytosphingosine

Carbohydr Res. 2018 Jun 30:463:1-5. doi: 10.1016/j.carres.2018.04.006. Epub 2018 Apr 13.

Authors

Arumugam Sankar¹, I-Cheng Chen¹, Shun-Yuan Luo²

Affiliations

¹ Department of Chemistry, National Chung Hsing University, 145 Xingda Rd., South Dist., Taichung City 402, Taiwan.
² Department of Chemistry, National Chung Hsing University, 145 Xingda Rd., South Dist., Taichung City 402, Taiwan. Electronic address: syluo@dragon.nchu.edu.tw.

PMID: 29689448
DOI: 10.1016/j.carres.2018.04.006

Abstract

A simple and efficient protocol for the synthesis of a sphingosine starting from cost-effective phytosphingosine has been described. Two alternative synthetic pathway have been disclosed based on the use of two different kinds of protective groups for the protection of the amino group in the phytosphingosine. The protected phytosphingosine was subsequently transformed into sphingosine in 5 steps i.e. protection of the amine group, protection of 1,3-diol, leaving group insertion, elimination, and one-pot deprotection.

Keywords: Deprotection; Elimination; Phytosphingosine; Protection; Regioselective; Sphingosine.

MeSH terms

Molecular Structure
Sphingosine / analogs & derivatives*
Sphingosine / chemical synthesis*
Sphingosine / chemistry
Stereoisomerism

Substances

phytosphingosine
Sphingosine