Efficient synthesis of deuterium- and tritium-labeled d-erythro-sphingosine

Deuterium‐ and tritium‐labeled d‐erythro‐sphingosine (1b and 1c) were prepared by an efficient approach based on a known stereoselective total synthesis. Tritium was introduced at C−1 by [3H]NaBH4 reduction in the final synthetic step to give 1c of high radiochemical purity. 1,1,3‐Trideuterio‐d‐eryt...

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Bibliographic Details
Published in:Journal of labelled compounds & radiopharmaceuticals 1999-09, Vol.42 (9), p.815-826
Main Authors: Li, Shengrong, Pang, Jihai, Wilson, William K., Schroepfer Jr, George J.
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
MTPA derivative
NMR
Organic chemistry
Preparations and properties
sphingosine
tritium labeling
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Summary:Deuterium‐ and tritium‐labeled d‐erythro‐sphingosine (1b and 1c) were prepared by an efficient approach based on a known stereoselective total synthesis. Tritium was introduced at C−1 by [3H]NaBH4 reduction in the final synthetic step to give 1c of high radiochemical purity. 1,1,3‐Trideuterio‐d‐erythro‐sphingosine (1b) was prepared similarly and showed >99·5% enantiomeric purity and a high level of deuterium incorporation. Copyright © 1999 John Wiley & Sons, Ltd.
ISSN:0362-4803
1099-1344
DOI:10.1002/(SICI)1099-1344(199909)42:9<815::AID-JLCR242>3.0.CO;2-2