Synthesis of ω-Methylsulfinyl- and ω-Methylsulfonylalkyl Glucosinolates
General pathways were devised to synthesize ω-methylsulfinyl- and ω-methylsulfonylalkyl glucosinolates, which represent an important class of structurally homogeneous plant specialized metabolites. The first approach was based on the selective <i>S</i>-oxidation of ω-methylsulfanyl analo...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-02-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/3/704 |
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| Summary: | General pathways were devised to synthesize ω-methylsulfinyl- and ω-methylsulfonylalkyl glucosinolates, which represent an important class of structurally homogeneous plant specialized metabolites. The first approach was based on the selective <i>S</i>-oxidation of ω-methylsulfanyl analogs previously obtained in our laboratory, producing the corresponding sulfoxide or sulfone counterparts in moderate yields. In an alternative approach, previously prepared ω-nitroalkyl methylsulfide precursors were selectively oxidized either to sulfoxides or to sulfones. The key-thiofunctionalized hydroximoyl chloride intermediates were prepared in situ from sulfoxides or sulfones using a nitronate chlorination strategy. A coupling reaction with 1-thio-β-<span style="font-variant: small-caps;">d</span>-glucopyranose was directly applied, followed by <i>O</i>-sulfation of the intermediate thiohydroximates. The final deprotection of the sugar moiety produced the target compounds, including renowned glucoraphanin and homologs, intended for further bioactivity investigations. |
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| ISSN: | 1420-3049 |