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Issue 14, 2000
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Practical syntheses of [13C]- and [14C]-labelled glucosphingolipids

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Abstract

Synthetic routes to [glucose-U-14C]-1-O-(β-D-glucopyranosyl)-N-stearoyl-D-erythro-sphingosine 1b and to [glucose-13C6]-1-O-(β-D-glucopyranosyl)sphingosine ([glucose-13C6]glucopsychosine, 2b) are described. Whereas the protected ceramide precursor for 1b was prepared using conventional methodology, two new strategies were developed in the course of the synthesis of 2b. Of these, one relies on keeping a protecting group in place at all times to avoid the handling difficulties associated with sphingosine 4, while the other generates a protected derivative (24) of sphingosine indirectly by means of a Mitsunobu inversion.

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Article information


Submitted
15 Mar 2000
Accepted
08 Jun 2000
First published
03 Jul 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2237-2242
Article type
Paper

Practical syntheses of [13C]- and [14C]-labelled glucosphingolipids

G. R. Duffin, G. J. Ellames, S. Hartmann, J. M. Herbert and D. I. Smith, J. Chem. Soc., Perkin Trans. 1, 2000, 2237
DOI: 10.1039/B002104K

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