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Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane–Sodium Iodide-Promoted Vorbrüggen Glycosylation
| dc.contributor.author | Mear, Sarah Jane | |
| dc.contributor.author | Nguyen, Long V | |
| dc.contributor.author | Rochford, Ashley J | |
| dc.contributor.author | Jamison, Timothy F | |
| dc.date.accessioned | 2022-03-09T15:48:51Z | |
| dc.date.available | 2022-03-09T15:48:51Z | |
| dc.date.issued | 2022-01-14 | |
| dc.identifier.uri | https://hdl.handle.net/1721.1/141085 | |
| dc.description.abstract | By simple combination of water and sodium iodide (NaI) with 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-oxathiolane 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 (±)-FTC/3TC from a tartrate diester. | en_US |
| dc.language.iso | en | |
| dc.publisher | American Chemical Society (ACS) | en_US |
| dc.relation.isversionof | 10.1021/acs.joc.1c02772 | en_US |
| dc.rights | Creative Commons Attribution-Noncommercial-Share Alike | en_US |
| dc.rights.uri | http://creativecommons.org/licenses/by-nc-sa/4.0/ | en_US |
| dc.source | chemRxiv | en_US |
| dc.title | Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane–Sodium Iodide-Promoted Vorbrüggen Glycosylation | en_US |
| dc.type | Article | en_US |
| dc.identifier.citation | Mear, Sarah Jane, Nguyen, Long V, Rochford, Ashley J and Jamison, Timothy F. 2022. "Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane–Sodium Iodide-Promoted Vorbrüggen Glycosylation." The Journal of Organic Chemistry. | |
| dc.relation.journal | The Journal of Organic Chemistry | en_US |
| dc.eprint.version | Original manuscript | en_US |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
| eprint.status | http://purl.org/eprint/status/NonPeerReviewed | en_US |
| dc.date.updated | 2022-03-09T15:40:53Z | |
| dspace.orderedauthors | Mear, SJ; Nguyen, LV; Rochford, AJ; Jamison, TF | en_US |
| dspace.date.submission | 2022-03-09T15:40:54Z | |
| mit.license | OPEN_ACCESS_POLICY | |
| mit.metadata.status | Authority Work and Publication Information Needed | en_US |
