Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint-Driven Innovation

[Image: see text] A new route was developed for construction of the oxathiolane intermediate used in the synthesis of lamivudine (3TC) and emtricitabine (FTC). We developed the presented route by constraining ourselves to low-cost, widely available starting materials—we refer to this as supply-cente...

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Autores principales: Kashinath, K., Snead, David R., Burns, Justina M., Stringham, Rodger W., Gupton, B. Frank, McQuade, D. Tyler
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7574620/
https://www.ncbi.nlm.nih.gov/pubmed/33100812
http://dx.doi.org/10.1021/acs.oprd.0c00145
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author Kashinath, K.
Snead, David R.
Burns, Justina M.
Stringham, Rodger W.
Gupton, B. Frank
McQuade, D. Tyler
author_facet Kashinath, K.
Snead, David R.
Burns, Justina M.
Stringham, Rodger W.
Gupton, B. Frank
McQuade, D. Tyler
author_sort Kashinath, K.
collection PubMed
description [Image: see text] A new route was developed for construction of the oxathiolane intermediate used in the synthesis of lamivudine (3TC) and emtricitabine (FTC). We developed the presented route by constraining ourselves to low-cost, widely available starting materials—we refer to this as supply-centered synthesis. Sulfenyl chloride chemistry was used to construct the framework for the oxathiolane from acyclic precursors. This bond construction choice enabled the use of chloroacetic acid, vinyl acetate, sodium thiosulfate, and water to produce the oxathiolane.
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spelling pubmed-75746202020-10-21 Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint-Driven Innovation Kashinath, K. Snead, David R. Burns, Justina M. Stringham, Rodger W. Gupton, B. Frank McQuade, D. Tyler Org Process Res Dev [Image: see text] A new route was developed for construction of the oxathiolane intermediate used in the synthesis of lamivudine (3TC) and emtricitabine (FTC). We developed the presented route by constraining ourselves to low-cost, widely available starting materials—we refer to this as supply-centered synthesis. Sulfenyl chloride chemistry was used to construct the framework for the oxathiolane from acyclic precursors. This bond construction choice enabled the use of chloroacetic acid, vinyl acetate, sodium thiosulfate, and water to produce the oxathiolane. American Chemical Society 2020-05-13 2020-10-16 /pmc/articles/PMC7574620/ /pubmed/33100812 http://dx.doi.org/10.1021/acs.oprd.0c00145 Text en This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Kashinath, K.
Snead, David R.
Burns, Justina M.
Stringham, Rodger W.
Gupton, B. Frank
McQuade, D. Tyler
Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint-Driven Innovation
title Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint-Driven Innovation
title_full Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint-Driven Innovation
title_fullStr Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint-Driven Innovation
title_full_unstemmed Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint-Driven Innovation
title_short Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint-Driven Innovation
title_sort synthesis of an oxathiolane drug substance intermediate guided by constraint-driven innovation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7574620/
https://www.ncbi.nlm.nih.gov/pubmed/33100812
http://dx.doi.org/10.1021/acs.oprd.0c00145
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