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New Synthesis of Diarylmethanes, Key Building Blocks for SGLT2 Inhibitors
[Image: see text] Synthesis of diarylmethanes, a key building block for SGLT2 inhibitors, has been developed through ketone synthesis by Friedel–Crafts acylation with TiCl(4), followed by reduction with TiCl(4)/NaBH(4). The new protocol proceeded more cleanly than the previous methods employing AlCl...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2023
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10193421/ https://www.ncbi.nlm.nih.gov/pubmed/37214716 http://dx.doi.org/10.1021/acsomega.3c01972 |
| _version_ | 1785043833948471296 |
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| author | Seki, Masahiko Tapkir, Sandeep Ramesharao Nadiveedhi, Maheshwara Reddy Mulani, Shaheen Kasim Mashima, Kazushi |
| author_facet | Seki, Masahiko Tapkir, Sandeep Ramesharao Nadiveedhi, Maheshwara Reddy Mulani, Shaheen Kasim Mashima, Kazushi |
| author_sort | Seki, Masahiko |
| collection | PubMed |
| description | [Image: see text] Synthesis of diarylmethanes, a key building block for SGLT2 inhibitors, has been developed through ketone synthesis by Friedel–Crafts acylation with TiCl(4), followed by reduction with TiCl(4)/NaBH(4). The new protocol proceeded more cleanly than the previous methods employing AlCl(3) and BF(3)·OEt(2)/Et(3)SiH to provide the diarylmethanes corresponding to canagliflozin, empagliflozin, and luseogliflozin in a highly expedient and affordable manner. In the case of a diarylmethane for the synthesis of dapagliflozin, the reduction step took place by an alternative method using InCl(3)/Al/BF(3)·OEt(2). |
| format | Online Article Text |
| id | pubmed-10193421 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2023 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-101934212023-05-19 New Synthesis of Diarylmethanes, Key Building Blocks for SGLT2 Inhibitors Seki, Masahiko Tapkir, Sandeep Ramesharao Nadiveedhi, Maheshwara Reddy Mulani, Shaheen Kasim Mashima, Kazushi ACS Omega [Image: see text] Synthesis of diarylmethanes, a key building block for SGLT2 inhibitors, has been developed through ketone synthesis by Friedel–Crafts acylation with TiCl(4), followed by reduction with TiCl(4)/NaBH(4). The new protocol proceeded more cleanly than the previous methods employing AlCl(3) and BF(3)·OEt(2)/Et(3)SiH to provide the diarylmethanes corresponding to canagliflozin, empagliflozin, and luseogliflozin in a highly expedient and affordable manner. In the case of a diarylmethane for the synthesis of dapagliflozin, the reduction step took place by an alternative method using InCl(3)/Al/BF(3)·OEt(2). American Chemical Society 2023-05-08 /pmc/articles/PMC10193421/ /pubmed/37214716 http://dx.doi.org/10.1021/acsomega.3c01972 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
| spellingShingle | Seki, Masahiko Tapkir, Sandeep Ramesharao Nadiveedhi, Maheshwara Reddy Mulani, Shaheen Kasim Mashima, Kazushi New Synthesis of Diarylmethanes, Key Building Blocks for SGLT2 Inhibitors |
| title | New Synthesis of
Diarylmethanes, Key Building Blocks
for SGLT2 Inhibitors |
| title_full | New Synthesis of
Diarylmethanes, Key Building Blocks
for SGLT2 Inhibitors |
| title_fullStr | New Synthesis of
Diarylmethanes, Key Building Blocks
for SGLT2 Inhibitors |
| title_full_unstemmed | New Synthesis of
Diarylmethanes, Key Building Blocks
for SGLT2 Inhibitors |
| title_short | New Synthesis of
Diarylmethanes, Key Building Blocks
for SGLT2 Inhibitors |
| title_sort | new synthesis of
diarylmethanes, key building blocks
for sglt2 inhibitors |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10193421/ https://www.ncbi.nlm.nih.gov/pubmed/37214716 http://dx.doi.org/10.1021/acsomega.3c01972 |
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