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Molecules 2018, 23(4), 786; https://doi.org/10.3390/molecules23040786

ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway

1
Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans et CNRS, UMR 7311, BP 6759, F-45067 Orléans CEDEX 2, France
2
Laboratoire IMRCP, UMR CNRS 5623, Université P. Sabatier Toulouse III, 118 route de Narbonne, 31062 Toulouse CEDEX 9, France
3
Department of Chemistry and Biochemistry, Biomolecular Sciences Programme, Laurentian University, Sudbury, ON P3E 2C6, Canada
*
Author to whom correspondence should be addressed.
Received: 9 March 2018 / Revised: 20 March 2018 / Accepted: 21 March 2018 / Published: 28 March 2018
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Abstract

A general pathway was devised to synthesize ω-methylsulfanylalkyl glucosinolates, which represent an important class of structurally homogeneous plant secondary metabolites. The required thiofunctionalized hydroximoyl chlorides were obtained from the corresponding α,ω-nitroalkyl methylsulfide precursors, involving as the key-step, a nitronate chlorination strategy. A coupling reaction with 1-thio-beta-d-glucopyranose, followed by O-sulfation of the intermediate thiohydroximate and final deprotection of the sugar moiety afforded the target compounds. View Full-Text
Keywords: glucosinolate; thiohydroximate; thiofunctionalized; nitronate glucosinolate; thiohydroximate; thiofunctionalized; nitronate
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Mavratzotis, M.; Cassel, S.; Montaut, S.; Rollin, P. ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway. Molecules 2018, 23, 786.

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