A facile and efficient synthesis of14C-labelled sulforaphane

Autor:	Christopher A. D'Souza, Dhimant Desai, Shantu Amin
Rok vydání:	2003
Předmět:	Thiophosgene Nitrile Chemistry Organic Chemistry Biochemistry Analytical Chemistry chemistry.chemical_compound Tosyl chloride Yield (chemistry) Drug Discovery Isothiocyanate Organic chemistry Radiology Nuclear Medicine and imaging Amine gas treating Hydrogen peroxide Spectroscopy Sulforaphane
Zdroj:	Journal of Labelled Compounds and Radiopharmaceuticals. 46:851-859
ISSN:	1099-1344 0362-4803
DOI:	10.1002/jlcr.724
Popis:	Isothiocyanates have gained considerable attention for their role as potent chemopreventive agents. Sulforaphane, 1a (SFN), a naturally occurring isothiocyanate, was isotopically labelled in five steps starting from 3-(methylthio)-1-propanol (2). Reacting 2 with tosyl chloride in the presence of Et3N yielded the tosylate 3. Gently refluxing 3 with K14CN in DMF gave the nitrile 4b. Reduction to the amine 5b was achieved using BH3-THF. Oxidation with 30% hydrogen peroxide followed by treatment with thiophosgene yielded (±)[1-14C]SFN, 1b. The overall radiochemical yield was 4.4% based on the starting K14CN. Copyright © 2003 John Wiley & Sons, Ltd.
Databáze:	OpenAIRE
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