A facile and efficient synthesis of 14C-labelled sulforaphane

Christopher A. D'Souza, Shantu Amin, Dhimant Desai

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

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 K 14CN 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 K 14CN.

Original languageEnglish (US)
Pages (from-to)851-859
Number of pages9
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume46
Issue number9
DOIs
StatePublished - Aug 1 2003

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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