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A facile method for steroid labeling by heavy isotopes of hydrogen

SYSNO ASEP	0446369
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	A facile method for steroid labeling by heavy isotopes of hydrogen
Author(s)	Marek, Aleš (UOCHB-X)_{RID, ORCID} Klepetářová, Blanka (UOCHB-X)_{RID, ORCID} Elbert, Tomáš (UOCHB-X)_{RID, ORCID}
Number of authors	3
Source Title	Tetrahedron. - : Elsevier - ISSN 0040-4020 Roč. 71, č. 29 (2015), s. 4874-4882
Number of pages	9 s.
Language	eng - English
Country	GB - United Kingdom
Keywords	brassinosteroids ; alpha-hydroxy ketones ; reductive dehalogenation ; tritium ; labeled compounds
Subject RIV	CC - Organic Chemistry
R&D Projects	IAA400550801 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR)
Institutional support	UOCHB-X - RVO:61388963
UT WOS	000357348100025
EID SCOPUS	84937407398
DOI	10.1016/j.tet.2015.04.099
Annotation	A new catalytic enantiospecific approach to the synthesis of epibrassinosteroids (and other polyhydroxylated steroids) regiospecifically labeled by heavy isotopes of hydrogen is reported. Chlorocarbonate, efficiently synthesized from a-hydroxy ketone by a reaction with triphosgene, undergoes reductive tritium dechlorination catalyzed by the [Pd-0]/Et3N system, providing 24-[3 beta-H-3]epicastasterone and 24-[3 beta-H-3]epibrassinolide, respectively, in good yield and with high specific activity (5.8 Ci/mmol; 20% tritium enrichment per molecule).
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2016

Number of the records: 1