A facile and efficient synthesis of 14C-labelled sulforaphane

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

Research output: Contribution to journalArticle

12 Citations (Scopus)

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

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Isothiocyanates
1-Propanol
Nitriles
Hydrogen Peroxide
Amines
Oxidation
sulforafan
4-toluenesulfonyl chloride
isothiocyanic acid
thiophosgene

All Science Journal Classification (ASJC) codes

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

Cite this

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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.",
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A facile and efficient synthesis of 14C-labelled sulforaphane. / D'Souza, Christopher A.; Amin, Shantu; Desai, Dhimant.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 46, No. 9, 01.08.2003, p. 851-859.

Research output: Contribution to journalArticle

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AU - Desai, Dhimant

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AB - 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.

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