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. 2019 Mar 29:15:811-817.
doi: 10.3762/bjoc.15.78. eCollection 2019.

Synthesis of acylglycerol derivatives by mechanochemistry

Affiliations

Synthesis of acylglycerol derivatives by mechanochemistry

Karen J Ardila-Fierro et al. Beilstein J Org Chem. .

Abstract

In recent times, many biologically relevant building blocks such as amino acids, peptides, saccharides, nucleotides and nucleosides, etc. have been prepared by mechanochemical synthesis. However, mechanosynthesis of lipids by ball milling techniques has remained essentially unexplored. In this work, a multistep synthetic route to access mono- and diacylglycerol derivatives by mechanochemistry has been realized, including the synthesis of diacylglycerol-coumarin conjugates.

Keywords: ball mill; coumarin; diacylglycerols; lipids; mechanochemistry.

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Figures

Figure 1
Figure 1
Biologically relevant molecules made, used or derivatized by mechanochemistry.
Figure 2
Figure 2
Isomeric diacyl-sn-glycerols (DAGs).
Scheme 1
Scheme 1
Synthetic route to access protected DAGs; PG = protecting group.
Scheme 2
Scheme 2
Protection of glycidol (1) with TBDMSCl in the ball mill. MM = mixer mill, PBM = planetary ball mill.
Scheme 3
Scheme 3
Cobalt-catalyzed epoxide ring-opening in the ball mill.
Scheme 4
Scheme 4
Mechanosynthesis of DAGs 5.
Scheme 5
Scheme 5
Conjugation of DAG 5a with 7-hydroxycoumarin (9).
Figure 3
Figure 3
UV−vis spectra of DAG 6a (dotted line) and conjugated DAGs 10a and 10a’ as a mixture (10a/10a’ 72:28) in toluene at a concentration of 0.5 μM.

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