The synthesis of sulfur‐ and selenium‐containing isosters of triacyl glycerols is herein described. Regioselective fluoride‐induced ring‐opening reaction of suitable substituted thiiranes with bis(trimethyl)silyl selenide, followed by in situ S‐ and Se‐acylation with fatty acid acyl chlorides, enables the one pot synthesis of mixed chalcogeno esters in good yield. The key step of this methodology is the functionalization of S‐Si and Se‐Si bonds of silyl chalcogenides, generated in situ under mild conditions. A related procedure for the synthesis of functionalized selenides, bearing two thiol ester and two ester moieties, was also developed through a fine tuning of the reaction conditions. The physico‐chemical properties of these novel fatty acid chalcogeno esters have been investigated through DSC, SAXS, WAXS, FTIR and polarized optical microscopy, and compared to those of the common triglycerides in order to highlight the effect of the replacement of oxygen with other calchogen elements in the polar head of the lipid.

Selenated and Sulfurated Analogues of Triacyl Glycerols: Selective Synthesis and Structural Characterization / Damiano Tanini, Veronica D'Esopo, Duccio Tatini, Moira Ambrosi, Pierandrea Lo Nostro, Antonella Capperucci. - In: CHEMISTRY. - ISSN 1521-3765. - ELETTRONICO. - 26:(2020), pp. 2719-2725. [10.1002/chem.201904686]

Selenated and Sulfurated Analogues of Triacyl Glycerols: Selective Synthesis and Structural Characterization

Damiano Tanini
;
Duccio Tatini;Moira Ambrosi;Pierandrea Lo Nostro;Antonella Capperucci
2020

Abstract

The synthesis of sulfur‐ and selenium‐containing isosters of triacyl glycerols is herein described. Regioselective fluoride‐induced ring‐opening reaction of suitable substituted thiiranes with bis(trimethyl)silyl selenide, followed by in situ S‐ and Se‐acylation with fatty acid acyl chlorides, enables the one pot synthesis of mixed chalcogeno esters in good yield. The key step of this methodology is the functionalization of S‐Si and Se‐Si bonds of silyl chalcogenides, generated in situ under mild conditions. A related procedure for the synthesis of functionalized selenides, bearing two thiol ester and two ester moieties, was also developed through a fine tuning of the reaction conditions. The physico‐chemical properties of these novel fatty acid chalcogeno esters have been investigated through DSC, SAXS, WAXS, FTIR and polarized optical microscopy, and compared to those of the common triglycerides in order to highlight the effect of the replacement of oxygen with other calchogen elements in the polar head of the lipid.
2020
26
2719
2725
Damiano Tanini, Veronica D'Esopo, Duccio Tatini, Moira Ambrosi, Pierandrea Lo Nostro, Antonella Capperucci
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1184887
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