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The Di-Tert-Butyl Oxymethylphosphonate Route to the Antiviral Drug Tenofovir

preprint
submitted on 15.09.2020 and posted on 16.09.2020 by Jule-Phillip Dietz, Dorota Ferenc, Timothy F. Jamison, B. Frank Gupton, Till Opatz
The present manuscript describes a simple, two step synthesis of tenofovir from HPA through phosphonomethalation with a novel doubly protected oxymethylphosphonate electrophile. The crystalline electrophile can be prepared in a simple reaction sequence and can be deblocked more easily than its ditehyl analogue involved in the current commercial process for making the drug.
The approach is general and can also be used for the preparation of related antivirals and the synthesis of adefovir is described as well.

Funding

Medicines 4 All Initiative

Bill and Melinda Gates Foundation

History

Email Address of Submitting Author

opatz@uni-mainz.de

Institution

Johannes Gutenberg University

Country

Germany

ORCID For Submitting Author

0000-0002-3266-4050

Declaration of Conflict of Interest

No conflict of interest to declare

Version Notes

Version Sep 15, 2020

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