Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir
Described herein is a novel Lewis acid catalyzed rearrangement–coupling of oxygen heterocycles and bis(diethylamino)chlorophosphine that provides direct formation of the phosphonomethyl ether functionality found in several important antiretroviral agents. A wide range of dioxolanes and 1,3-dioxanes...
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2016
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| Online Access: | http://hdl.handle.net/1721.1/105334 https://orcid.org/0000-0002-4140-8315 https://orcid.org/0000-0002-8601-7799 |
| _version_ | 1826203231165874176 |
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| author | Ocampo, Charles Edward Lee, Doris Jamison, Timothy F |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Ocampo, Charles Edward Lee, Doris Jamison, Timothy F |
| author_sort | Ocampo, Charles Edward |
| collection | MIT |
| description | Described herein is a novel Lewis acid catalyzed rearrangement–coupling of oxygen heterocycles and bis(diethylamino)chlorophosphine that provides direct formation of the phosphonomethyl ether functionality found in several important antiretroviral agents. A wide range of dioxolanes and 1,3-dioxanes may be employed, furnishing the desired products in good yield. The utility of this method is demonstrated in a novel synthesis of tenofovir, an antiretroviral drug used in the treatment of HIV/AIDS and hepatitis B. |
| first_indexed | 2024-09-23T12:33:23Z |
| format | Article |
| id | mit-1721.1/105334 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T12:33:23Z |
| publishDate | 2016 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1053342022-09-28T08:37:12Z Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir Ocampo, Charles Edward Lee, Doris Jamison, Timothy F Massachusetts Institute of Technology. Department of Chemistry Jamison, Timothy F Ocampo, Charles Edward Lee, Doris Jamison, Timothy F Described herein is a novel Lewis acid catalyzed rearrangement–coupling of oxygen heterocycles and bis(diethylamino)chlorophosphine that provides direct formation of the phosphonomethyl ether functionality found in several important antiretroviral agents. A wide range of dioxolanes and 1,3-dioxanes may be employed, furnishing the desired products in good yield. The utility of this method is demonstrated in a novel synthesis of tenofovir, an antiretroviral drug used in the treatment of HIV/AIDS and hepatitis B. Bill & Melinda Gates Foundation (“Medicines for All” Initiative) Natural Sciences and Engineering Research Council of Canada (NSERC Postdoctoral Fellowship) 2016-11-15T20:00:07Z 2016-11-15T20:00:07Z 2015-02 2014-12 Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 http://hdl.handle.net/1721.1/105334 Ocampo, Charles E., Doris Lee, and Timothy F. Jamison. “Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir.” Organic Letters 17, no. 4 (February 20, 2015): 820-823. https://orcid.org/0000-0002-4140-8315 https://orcid.org/0000-0002-8601-7799 en_US http://dx.doi.org/10.1021/ol503612h Organic Letters Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) Prof. Jamison via Erja Kajosalo |
| spellingShingle | Ocampo, Charles Edward Lee, Doris Jamison, Timothy F Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir |
| title | Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir |
| title_full | Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir |
| title_fullStr | Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir |
| title_full_unstemmed | Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir |
| title_short | Selective Lewis Acid Catalyzed Assembly of Phosphonomethyl Ethers: Three-Step Synthesis of Tenofovir |
| title_sort | selective lewis acid catalyzed assembly of phosphonomethyl ethers three step synthesis of tenofovir |
| url | http://hdl.handle.net/1721.1/105334 https://orcid.org/0000-0002-4140-8315 https://orcid.org/0000-0002-8601-7799 |
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