Issue 6, 2006
From the journal:

Organic & Biomolecular Chemistry

A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs

Ye Cai,a   Chang-Chun Linga  and  David R. Bundle*a  

* Corresponding authors

a Alberta Ingenuity Center for Carbohydrate Science, Department of Chemistry, University of Alberta, Edmonton, Canada
E-mail: dave.bundle@ualberta.ca

Abstract

Sphingosine, sphinganines and phytosphingosines and their analogs were synthesized by an aldol condensation between an iminoglycinate bearing a (+)-(1R,2R,5R)-2-hydroxy-3-pinanone group as chiral auxiliary and an appropriate aldehyde. All condensations proceeded with excellent enantioselectivity to generate the (2S,3R)-D-erythro structures in good yields.

Graphical abstract: A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs

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Article information

DOI
https://doi.org/10.1039/B516333A
Article type
Paper
Submitted
17 Nov 2005
Accepted
04 Jan 2006
First published
26 Jan 2006

Org. Biomol. Chem., 2006,4, 1140-1146

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A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs

Y. Cai, C. Ling and D. R. Bundle, Org. Biomol. Chem., 2006, 4, 1140 DOI: 10.1039/B516333A

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