Synthesis of Cyclic Diglycerols: The Utility of the BF3·OEt2-Mediated Intramolecular Epoxide Ring-Opening Reaction for the Cyclic Polyglycerol Synthesis.

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We reported the synthesis of cyclic diglycerol, which was the minimum unit in polyglycerols. Epoxy alcohols of a linear diglycerol were treated with catalytic amount of boron trifluoride etherate (BF3·OEt2) in high diluted dichloromethane (CH2Cl2) to give the corresponding 1,4-dioxepane and 1,4-dioxane type cyclic diglycerols in high yield as a single structural isomer. The structures of the cyclic products were determined by 1D and 2D NMR spectral analysis. The results investigated the cyclization were dominated to Baldwin’s rule. The synthesized cyclic diglycerol can use as a standard.