Stereoselective synthesis of new glycooxathiecinone using vic-cyclic thionocarbonate haloalkylation and ring closing metathesis as key steps |
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Authors: | Mohammed Benazza Rami Kanso Gilles Demailly |
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Institution: | Laboratoire des Glucides UMR 6219-CNRS, Université de Picardie Jules Verne, 33 Rue Saint-Leu, 80039 Amiens Cedex, France |
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Abstract: | Herein, we describe the first glycoconjugate macrocyclic thiolcarbonate namely (Z)-10(S)-3′-O-acetyl-1′,2′-O-isopropylidene-4′-deoxy-d-erythrofuranose]-4,7,9-trihydro-10H-8-thia-1,3-oxathiecin-2-one (17a) using a strategy based on two key steps synthesis: (i) a haloalkylation of vic-diol via their cyclic thionocarbonate derivatives; (ii) a macrocyclisation using ring closing metathesis reaction. Detailed here is a newly developed extension of vic-diol halogenation via the cyclic thionocarbonate function but using a range of alkyl halides other than the customarily used MeI. For example, with 1,2-O-isopropylidene-5,6-O-thionocarbonate-d-glucose (1) and allyl bromide, the 5-allylthiolcarbonate-6-bromo-6-deoxy-d-glucose derivative 6 was obtained in good yield. The later submitted to 6-allythioetherification and ring closing metathesis (RCM) with Grubbs second generation gave stereoselectively the target oxathiecinone 17a in 75% yield for the RCM step. |
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Keywords: | Cylic thionocarbonate Thiolcarbonate Glycooxathiecinone Metathesis Haloalkylation Antioxidant |
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