Short and Stereocontrolled Cyclic Polyglycerols Synthesis Using BF3·OEt2 Mediated Intramolecular Epoxide-Opening Reaction
摘要:
We developed a new method for the stereocontrolled synthesis of cyclic oligoglycerols. Optically pure solketal and epichlorohydrin were coupled with allyl alcohol under aqueous basic conditions to construct a linear triglycerol skeleton. After subsequent steps, the epoxy alcohol (7) obtained was treated with a catalytic amount of BF3 center dot OEt2 in CH2Cl2 to produce in a high yield of the desired cyclic triglycerol through a regioselective, intramolecular epoxide ring-opening reaction.
We developed a new method for the stereocontrolled synthesis of cyclic oligoglycerols. Optically pure solketal and epichlorohydrin were coupled with allyl alcohol under aqueous basic conditions to construct a linear triglycerol skeleton. After subsequent steps, the epoxy alcohol (7) obtained was treated with a catalytic amount of BF3 center dot OEt2 in CH2Cl2 to produce in a high yield of the desired cyclic triglycerol through a regioselective, intramolecular epoxide ring-opening reaction.