The development of C—S bond-forming methods is of significant importance. Multiple reports have confirmed that the tetrahydrothiophene moiety is present in various biologically active molecules that possess anti-inflammatory, anti-viral, and anti-cancer properties. Recently, Robertson et al. reported a facile, enantioselective, and intramolecular synthesis of tetrahydrothiophenes starting from a phosphorothioate ester that possessed a tethered chiral alcohol. This previously reported methodology is currently being applied to the enantioselective synthesis of 5-substituted-1,3-oxathiolanes. The 1,3-oxathiolane moiety is of interest as it is present in biologically active molecules such as Lamivudine, which is an antiretroviral therapeutic used in the treatment of HIV/AIDS, while Cevimeline is a muscarinic agonist used to treat dry mouth caused by Sjögren’s syndrome. The current methodology describes the synthesis of the common intermediate O,O-diethyl S-((2-(methoxy(methyl)amino)-2-oxoethoxy)methyl) phosphorothioate, which will be utilized for the preparation of a library of chiral 1,3-oxathiolanes.

Facile synthesis of chiral 5-substituted 1,3-oxathiolanes

251st National Meeting (2016)

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