Modular and Stereoselective Synthesis of C‑Aryl Glycosides via Catellani Reaction

Modular and Stereoselective Synthesis of C‑Aryl Glycosides via Catellani Reaction

In this work, we describe a Catellani-type C–H glycosylation to provide rapid access to various highly decorated α-C-(hetero)­aryl glycosides in a modular and stereoselective manner (>90 examples). The termination step is flexible, which is demonstrated by ipso-Heck reaction, hydrogenation, Suzuk...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2020-09, Vol.142 (35), p.14864-14870
Hauptverfasser: Lv, Weiwei, Chen, Yanhui, Wen, Si, Ba, Dan, Cheng, Guolin
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 14870
container_issue 35
container_start_page 14864
container_title Journal of the American Chemical Society
container_volume 142
creator Lv, Weiwei
Chen, Yanhui
Wen, Si
Ba, Dan
Cheng, Guolin
description In this work, we describe a Catellani-type C–H glycosylation to provide rapid access to various highly decorated α-C-(hetero)­aryl glycosides in a modular and stereoselective manner (>90 examples). The termination step is flexible, which is demonstrated by ipso-Heck reaction, hydrogenation, Suzuki coupling, and Sonogashira coupling. Application of this methodology has been showcased by preparing glycoside–pharmacophore conjugates and a dapagliflozin analogue. Notably, the technology developed herein represents an unprecedented example of Catellani-type alkylation involving an SN1 pathway.
doi_str_mv 10.1021/jacs.0c07634
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2435189920</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2435189920</sourcerecordid><originalsourceid>FETCH-LOGICAL-a324t-6668fc54beda34a37e85166caea2e686bae891058711913e512110f560b036bb3</originalsourceid><addsrcrecordid>eNptkE9Lw0AQxRdRbK3ePMsePZi6f5LN5liKVqEiWD2HyWaCKWm27iaF3PwKfkU_iamtevE0DPzem3mPkHPOxpwJfr0E48fMsFjJ8IAMeSRYEHGhDsmQMSaCWCs5ICfeL_s1FJofk4EUmuk41kOyeLB5W4GjUOd00aBD67FC05QbpIuubl7Rl57agk4_3z8mrqvorOqM9WWOnm5KoFNosKqgLukTQq-z9Sk5KqDyeLafI_Jye_M8vQvmj7P76WQegBRhEyildGGiMMMcZAgyRh1xpQwgCFRaZYA64SzSMecJl9iH4pwVkWIZkyrL5Ihc7nzXzr616Jt0VXrz_Qza1qcilBHXSSJYj17tUOOs9w6LdO3KFbgu5Szd1phua0z3Nfb4xd65zVaY_8I_vf2d3qqWtnV1H_R_ry99zXuA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2435189920</pqid></control><display><type>article</type><title>Modular and Stereoselective Synthesis of C‑Aryl Glycosides via Catellani Reaction</title><source>American Chemical Society Journals</source><creator>Lv, Weiwei ; Chen, Yanhui ; Wen, Si ; Ba, Dan ; Cheng, Guolin</creator><creatorcontrib>Lv, Weiwei ; Chen, Yanhui ; Wen, Si ; Ba, Dan ; Cheng, Guolin</creatorcontrib><description>In this work, we describe a Catellani-type C–H glycosylation to provide rapid access to various highly decorated α-C-(hetero)­aryl glycosides in a modular and stereoselective manner (&gt;90 examples). The termination step is flexible, which is demonstrated by ipso-Heck reaction, hydrogenation, Suzuki coupling, and Sonogashira coupling. Application of this methodology has been showcased by preparing glycoside–pharmacophore conjugates and a dapagliflozin analogue. Notably, the technology developed herein represents an unprecedented example of Catellani-type alkylation involving an SN1 pathway.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.0c07634</identifier><identifier>PMID: 32808778</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of the American Chemical Society, 2020-09, Vol.142 (35), p.14864-14870</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a324t-6668fc54beda34a37e85166caea2e686bae891058711913e512110f560b036bb3</citedby><cites>FETCH-LOGICAL-a324t-6668fc54beda34a37e85166caea2e686bae891058711913e512110f560b036bb3</cites><orcidid>0000-0003-1013-2456</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jacs.0c07634$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jacs.0c07634$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32808778$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lv, Weiwei</creatorcontrib><creatorcontrib>Chen, Yanhui</creatorcontrib><creatorcontrib>Wen, Si</creatorcontrib><creatorcontrib>Ba, Dan</creatorcontrib><creatorcontrib>Cheng, Guolin</creatorcontrib><title>Modular and Stereoselective Synthesis of C‑Aryl Glycosides via Catellani Reaction</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>In this work, we describe a Catellani-type C–H glycosylation to provide rapid access to various highly decorated α-C-(hetero)­aryl glycosides in a modular and stereoselective manner (&gt;90 examples). The termination step is flexible, which is demonstrated by ipso-Heck reaction, hydrogenation, Suzuki coupling, and Sonogashira coupling. Application of this methodology has been showcased by preparing glycoside–pharmacophore conjugates and a dapagliflozin analogue. Notably, the technology developed herein represents an unprecedented example of Catellani-type alkylation involving an SN1 pathway.</description><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNptkE9Lw0AQxRdRbK3ePMsePZi6f5LN5liKVqEiWD2HyWaCKWm27iaF3PwKfkU_iamtevE0DPzem3mPkHPOxpwJfr0E48fMsFjJ8IAMeSRYEHGhDsmQMSaCWCs5ICfeL_s1FJofk4EUmuk41kOyeLB5W4GjUOd00aBD67FC05QbpIuubl7Rl57agk4_3z8mrqvorOqM9WWOnm5KoFNosKqgLukTQq-z9Sk5KqDyeLafI_Jye_M8vQvmj7P76WQegBRhEyildGGiMMMcZAgyRh1xpQwgCFRaZYA64SzSMecJl9iH4pwVkWIZkyrL5Ihc7nzXzr616Jt0VXrz_Qza1qcilBHXSSJYj17tUOOs9w6LdO3KFbgu5Szd1phua0z3Nfb4xd65zVaY_8I_vf2d3qqWtnV1H_R_ry99zXuA</recordid><startdate>20200902</startdate><enddate>20200902</enddate><creator>Lv, Weiwei</creator><creator>Chen, Yanhui</creator><creator>Wen, Si</creator><creator>Ba, Dan</creator><creator>Cheng, Guolin</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1013-2456</orcidid></search><sort><creationdate>20200902</creationdate><title>Modular and Stereoselective Synthesis of C‑Aryl Glycosides via Catellani Reaction</title><author>Lv, Weiwei ; Chen, Yanhui ; Wen, Si ; Ba, Dan ; Cheng, Guolin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a324t-6668fc54beda34a37e85166caea2e686bae891058711913e512110f560b036bb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lv, Weiwei</creatorcontrib><creatorcontrib>Chen, Yanhui</creatorcontrib><creatorcontrib>Wen, Si</creatorcontrib><creatorcontrib>Ba, Dan</creatorcontrib><creatorcontrib>Cheng, Guolin</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lv, Weiwei</au><au>Chen, Yanhui</au><au>Wen, Si</au><au>Ba, Dan</au><au>Cheng, Guolin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Modular and Stereoselective Synthesis of C‑Aryl Glycosides via Catellani Reaction</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2020-09-02</date><risdate>2020</risdate><volume>142</volume><issue>35</issue><spage>14864</spage><epage>14870</epage><pages>14864-14870</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>In this work, we describe a Catellani-type C–H glycosylation to provide rapid access to various highly decorated α-C-(hetero)­aryl glycosides in a modular and stereoselective manner (&gt;90 examples). The termination step is flexible, which is demonstrated by ipso-Heck reaction, hydrogenation, Suzuki coupling, and Sonogashira coupling. Application of this methodology has been showcased by preparing glycoside–pharmacophore conjugates and a dapagliflozin analogue. Notably, the technology developed herein represents an unprecedented example of Catellani-type alkylation involving an SN1 pathway.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>32808778</pmid><doi>10.1021/jacs.0c07634</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-1013-2456</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2020-09, Vol.142 (35), p.14864-14870
issn 0002-7863
1520-5126
language eng
recordid cdi_proquest_miscellaneous_2435189920
source American Chemical Society Journals
title Modular and Stereoselective Synthesis of C‑Aryl Glycosides via Catellani Reaction
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-01T04%3A17%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Modular%20and%20Stereoselective%20Synthesis%20of%20C%E2%80%91Aryl%20Glycosides%20via%20Catellani%20Reaction&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Lv,%20Weiwei&rft.date=2020-09-02&rft.volume=142&rft.issue=35&rft.spage=14864&rft.epage=14870&rft.pages=14864-14870&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/jacs.0c07634&rft_dat=%3Cproquest_cross%3E2435189920%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2435189920&rft_id=info:pmid/32808778&rfr_iscdi=true