通过环状硫酸酯中间体从D-核糖植物鞘氨醇高效合成D-赤藓糖型鞘氨醇和D-赤藓糖型叠氮鞘氨醇。

Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate.

作者信息

Kim Sanghee, Lee Sukjin, Lee Taeho, Ko Hyojin, Kim Deukjoon

机构信息

College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea.

出版信息

J Org Chem. 2006 Oct 27;71(22):8661-4. doi: 10.1021/jo0614543.

DOI:10.1021/jo0614543

PMID:17064054

Abstract

The synthesis of naturally occurring d-erythro-sphingosine and synthetically useful D-erythro-2-azidosphingosine 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.

摘要

本文描述了从市售的d-核糖基植物鞘氨醇合成天然存在的d-赤藓糖型鞘氨醇以及具有合成用途的D-赤藓糖型-2-叠氮基鞘氨醇的方法。该合成方法的一个重要特征是通过环状硫酸酯中间体将植物鞘氨醇的3,4-邻二醇选择性转化为鞘氨醇特有的E-烯丙醇。