Gaware, S;
Kori, S;
Serrano, JL;
Dandela, R;
Hilton, S;
Sanghvi, YS;
Kapdi, AR;
(2023)
Rapid plugged flow synthesis of nucleoside analogues via Suzuki-Miyaura coupling and heck Alkenylation of 5-Iodo-2’-deoxyuridine (or cytidine).
Journal of Flow Chemistry
, 13
pp. 293-310.
10.1007/s41981-023-00265-1.
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Abstract
Nucleosides modification via conventional cross-coupling has been performed using different catalytic systems and found to take place via long reaction times. However, since the pandemic, nucleoside-based antivirals and vaccines have received widespread attention and the requirement for rapid modification and synthesis of these moieties has become a major objective for researchers. To address this challenge, we describe the development of a rapid flow-based cross-coupling synthesis protocol for a variety of C5-pyrimidine substituted nucleosides. The protocol allows for facile access to multiple nucleoside analogues in very good yields in a few minutes compared to conventional batch chemistry. To highlight the utility of our approach, the synthesis of an anti-HSV drug, BVDU was also achieved in an efficient manner using our new protocol. Graphical abstract: [Figure not available: see fulltext.]
Type: | Article |
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Title: | Rapid plugged flow synthesis of nucleoside analogues via Suzuki-Miyaura coupling and heck Alkenylation of 5-Iodo-2’-deoxyuridine (or cytidine) |
Open access status: | An open access version is available from UCL Discovery |
DOI: | 10.1007/s41981-023-00265-1 |
Publisher version: | https://doi.org/10.1007/s41981-023-00265-1 |
Language: | English |
Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
Keywords: | Nucleosides, Plugged flow, Antiviral, Cross-Coupling |
UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry |
URI: | https://discovery-pp.ucl.ac.uk/id/eprint/10168670 |
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