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Article

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)
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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MDPI and ACS Style

Mavratzotis, M.; Cassel, S.; Montaut, S.; Rollin, P. ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway. Molecules 2018, 23, 786. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules23040786

AMA Style

Mavratzotis M, Cassel S, Montaut S, Rollin P. ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway. Molecules. 2018; 23(4):786. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules23040786

Chicago/Turabian Style

Mavratzotis, Manolis, Stéphanie Cassel, Sabine Montaut, and Patrick Rollin. 2018. "ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway" Molecules 23, no. 4: 786. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules23040786

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