Literature DB >> 26061009

Synthesis of 6-Hydroxysphingosine and α-Hydroxy Ceramide Using a Cross-Metathesis Strategy.

Patrick Wisse1, Mark A R de Geus1, Gen Cross1, Adrianus M C H van den Nieuwendijk1, Eva J van Rooden1, Richard J B H N van den Berg1, Johannes M F G Aerts1, Gijsbert A van der Marel1, Jeroen D C Codée1, Herman S Overkleeft1.   

Abstract

In this paper, a new synthetic route toward 6-hydroxysphingosine and α-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.

Entities:  

Mesh:

Substances:

Year:  2015        PMID: 26061009     DOI: 10.1021/acs.joc.5b00823

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  1 in total

1.  Structural and Functional Analysis of Bacterial Sulfonosphingolipids and Rosette-Inducing Factor 2 (RIF-2) by Mass Spectrometry-Guided Isolation and Total Synthesis.

Authors:  Daniel Leichnitz; Chia-Chi Peng; Luka Raguž; Florentine U N Rutaganira; Theresa Jautzus; Lars Regestein; Nicole King; Christine Beemelmanns
Journal:  Chemistry       Date:  2021-12-28       Impact factor: 5.020

  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.