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Abstract
By simply adding water and sodium iodide (NaI) to chlorotrimethylsilane (TMSCl), promotion of a Vorbrüggen glycosylation en route to essential HIV drugs emtricitabine (FTC) and lamivudine (3TC) is achieved. TMSCl-NaI in wet solvent (0.1 M water) activates a 1,3-oxathiolanyl acetate donor for N-glycosylation of silylated cytosine derivatives, leading to cis ox-athiolane products with up to 95% yield and >20:1 dr. This telescoped sequence is followed by recrystallization and borohydride reduction, resulting in rapid synthesis of rac-FTC/3TC from an achiral tartrate ester.
Supplementary materials
Title
Supporting Information for Synthesis of rac-Emtricitabine and rac-Lamivudine by Chlorotri-methylsilane-Sodium Iodide Promoted Vorbrüggen Glycosylation
Description
Supplementary methods, synthetic schemes, HPLC traces, and NMR spectra supporting findings disclosed in the accompanying manuscript.
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