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Efficient synthesis of deuterium‐ and tritium‐labeled d ‐ erythro ‐sphingosine
Author(s) -
Li Shengrong,
Pang Jihai,
Wilson William K.,
Schroepfer George J.
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199909)42:9<815::aid-jlcr242>3.0.co;2-2
Subject(s) - chemistry , tritium , sphingosine , deuterium , diastereomer , enantiomer , radiochemistry , stereoselectivity , organic chemistry , nuclear physics , catalysis , biochemistry , physics , receptor
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 [ 3 H]NaBH 4 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.