Synthesis of 28,28,28-trideutero-25-hydroxydihydrotachysterol2

[Display omitted] •A convergent synthesis of the 28,28,28-trideutero-25-hydroxydihydrotachysterol2 was achieved.•Isotope labeling was introduced through a syn-SN2’ allylic substituton with lithium deuterocuprate.•The construction/formation of the diene system was done by the Wittig-Horner approach.•...

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Bibliographic Details
Published inThe Journal of steroid biochemistry and molecular biology Vol. 185; pp. 248 - 250
Main Authors Sigüeiro, Rita, Loureiro, Julian, González-Berdullas, Patricia, Mouriño, Antonio, Maestro, Miguel A.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.01.2019
Subjects
25-Hydroxydihydrotachysterol2
Labeled compounds
Synthesis
Vitamin D
Synthesis
Vitamin D
25-Hydroxydihydrotachysterol2
Labeled compounds
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Summary:[Display omitted] •A convergent synthesis of the 28,28,28-trideutero-25-hydroxydihydrotachysterol2 was achieved.•Isotope labeling was introduced through a syn-SN2’ allylic substituton with lithium deuterocuprate.•The construction/formation of the diene system was done by the Wittig-Horner approach.•28,28,28-Trideutero-25-hydroxydihydrotachysterol2 has been used as a internal standard for HPLC/MS. As part of our program on synthesis of labeled vitamin D metabolites and analogs, we describe here an efficient and versatile synthetic approach to 28,28,28-trideutero- 25-hydroxydihydrotachysterol2 where isotopic labeling was incorporated stereoselectively in the last step of the synthesis. This deuterated compound will allow the study this analog in vitro or in vivo and to measure AT10-like compounds in serum by LC–MS/MS.
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ISSN:0960-0760
1879-1220
DOI:10.1016/j.jsbmb.2018.09.014