Direct N‐Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co‐Catalysis
Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides, including the asparagine residues of several peptides, were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylor...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2018-03, Vol.57 (14), p.3646-3650 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3650 |
|---|---|
| container_issue | 14 |
| container_start_page | 3646 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 57 |
| creator | Kobayashi, Yusuke Nakatsuji, Yuya Li, Shanji Tsuzuki, Seiji Takemoto, Yoshiji |
| description | Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides, including the asparagine residues of several peptides, were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylorthoamides, including rearrangement to the corresponding β‐N‐glycoside, were also demonstrated.
Transformation of amides: Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylorthoamides, including rearrangement to the corresponding β‐N‐glycosides, were also demonstrated. |
| doi_str_mv | 10.1002/anie.201712726 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1999193792</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1999193792</sourcerecordid><originalsourceid>FETCH-LOGICAL-c5606-c8ec15988bc86e0524df820b89f3ec9b4b39a476f5a824e196b2b6de4bed73df3</originalsourceid><addsrcrecordid>eNqF0b1uFDEUBWALgUhI0lIiSzQ0s_HPzNgul01IIkWhWWrL9txhHXnHwZ5RNChFHoFn5EnwsiFINFS-xedj-R6E3lKyoISwUzN4WDBCBWWCtS_QIW0YrbgQ_GWZa84rIRt6gN7kfFu8lKR9jQ6YqimrFT9ED2c-gRvxzc_HHxdhdrGfBjf6OJjgv5vdgGOPl1vfQcb3ftzg3yrPAa-Td5sQUzQORl-EGQHbGa83Pk4JzOmlCfErDPhjHDp8FoeY8CqWd1ZmNGHOPh-jV70JGU6eziP05dP5enVZXX--uFotryvXtKStnARHGyWldbIF0rC66yUjVqqeg1O2tlyZWrR9YySrgarWMtt2UFvoBO96foQ-7HPvUvw2QR711mcHIZgB4pQ1VUpRxYVihb7_h96Wz5RtZL3bcllzI2RRi71yKeacoNd3yW9NmjUleteL3vWin3spF949xU52C90z_1NEAWoP7n2A-T9xenlzdf43_Bemz52C</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2017712578</pqid></control><display><type>article</type><title>Direct N‐Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co‐Catalysis</title><source>Access via Wiley Online Library</source><creator>Kobayashi, Yusuke ; Nakatsuji, Yuya ; Li, Shanji ; Tsuzuki, Seiji ; Takemoto, Yoshiji</creator><creatorcontrib>Kobayashi, Yusuke ; Nakatsuji, Yuya ; Li, Shanji ; Tsuzuki, Seiji ; Takemoto, Yoshiji</creatorcontrib><description>Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides, including the asparagine residues of several peptides, were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylorthoamides, including rearrangement to the corresponding β‐N‐glycoside, were also demonstrated.
Transformation of amides: Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylorthoamides, including rearrangement to the corresponding β‐N‐glycosides, were also demonstrated.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201712726</identifier><identifier>PMID: 29412493</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Amides ; Asparagine ; Brønsted acid catalysis ; carbohydrates ; Catalysis ; Catalysts ; glycosylation ; organocatalysis ; Peptides ; Thiourea ; Thioureas</subject><ispartof>Angewandte Chemie International Edition, 2018-03, Vol.57 (14), p.3646-3650</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5606-c8ec15988bc86e0524df820b89f3ec9b4b39a476f5a824e196b2b6de4bed73df3</citedby><cites>FETCH-LOGICAL-c5606-c8ec15988bc86e0524df820b89f3ec9b4b39a476f5a824e196b2b6de4bed73df3</cites><orcidid>0000-0003-3074-7378 ; 0000-0003-1375-3821</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201712726$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201712726$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29412493$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kobayashi, Yusuke</creatorcontrib><creatorcontrib>Nakatsuji, Yuya</creatorcontrib><creatorcontrib>Li, Shanji</creatorcontrib><creatorcontrib>Tsuzuki, Seiji</creatorcontrib><creatorcontrib>Takemoto, Yoshiji</creatorcontrib><title>Direct N‐Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co‐Catalysis</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides, including the asparagine residues of several peptides, were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylorthoamides, including rearrangement to the corresponding β‐N‐glycoside, were also demonstrated.
Transformation of amides: Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylorthoamides, including rearrangement to the corresponding β‐N‐glycosides, were also demonstrated.</description><subject>Amides</subject><subject>Asparagine</subject><subject>Brønsted acid catalysis</subject><subject>carbohydrates</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>glycosylation</subject><subject>organocatalysis</subject><subject>Peptides</subject><subject>Thiourea</subject><subject>Thioureas</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqF0b1uFDEUBWALgUhI0lIiSzQ0s_HPzNgul01IIkWhWWrL9txhHXnHwZ5RNChFHoFn5EnwsiFINFS-xedj-R6E3lKyoISwUzN4WDBCBWWCtS_QIW0YrbgQ_GWZa84rIRt6gN7kfFu8lKR9jQ6YqimrFT9ED2c-gRvxzc_HHxdhdrGfBjf6OJjgv5vdgGOPl1vfQcb3ftzg3yrPAa-Td5sQUzQORl-EGQHbGa83Pk4JzOmlCfErDPhjHDp8FoeY8CqWd1ZmNGHOPh-jV70JGU6eziP05dP5enVZXX--uFotryvXtKStnARHGyWldbIF0rC66yUjVqqeg1O2tlyZWrR9YySrgarWMtt2UFvoBO96foQ-7HPvUvw2QR711mcHIZgB4pQ1VUpRxYVihb7_h96Wz5RtZL3bcllzI2RRi71yKeacoNd3yW9NmjUleteL3vWin3spF949xU52C90z_1NEAWoP7n2A-T9xenlzdf43_Bemz52C</recordid><startdate>20180326</startdate><enddate>20180326</enddate><creator>Kobayashi, Yusuke</creator><creator>Nakatsuji, Yuya</creator><creator>Li, Shanji</creator><creator>Tsuzuki, Seiji</creator><creator>Takemoto, Yoshiji</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3074-7378</orcidid><orcidid>https://orcid.org/0000-0003-1375-3821</orcidid></search><sort><creationdate>20180326</creationdate><title>Direct N‐Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co‐Catalysis</title><author>Kobayashi, Yusuke ; Nakatsuji, Yuya ; Li, Shanji ; Tsuzuki, Seiji ; Takemoto, Yoshiji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5606-c8ec15988bc86e0524df820b89f3ec9b4b39a476f5a824e196b2b6de4bed73df3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Amides</topic><topic>Asparagine</topic><topic>Brønsted acid catalysis</topic><topic>carbohydrates</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>glycosylation</topic><topic>organocatalysis</topic><topic>Peptides</topic><topic>Thiourea</topic><topic>Thioureas</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kobayashi, Yusuke</creatorcontrib><creatorcontrib>Nakatsuji, Yuya</creatorcontrib><creatorcontrib>Li, Shanji</creatorcontrib><creatorcontrib>Tsuzuki, Seiji</creatorcontrib><creatorcontrib>Takemoto, Yoshiji</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kobayashi, Yusuke</au><au>Nakatsuji, Yuya</au><au>Li, Shanji</au><au>Tsuzuki, Seiji</au><au>Takemoto, Yoshiji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct N‐Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co‐Catalysis</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-03-26</date><risdate>2018</risdate><volume>57</volume><issue>14</issue><spage>3646</spage><epage>3650</epage><pages>3646-3650</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides, including the asparagine residues of several peptides, were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylorthoamides, including rearrangement to the corresponding β‐N‐glycoside, were also demonstrated.
Transformation of amides: Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylorthoamides, including rearrangement to the corresponding β‐N‐glycosides, were also demonstrated.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29412493</pmid><doi>10.1002/anie.201712726</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-3074-7378</orcidid><orcidid>https://orcid.org/0000-0003-1375-3821</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2018-03, Vol.57 (14), p.3646-3650 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1999193792 |
| source | Access via Wiley Online Library |
| subjects | Amides Asparagine Brønsted acid catalysis carbohydrates Catalysis Catalysts glycosylation organocatalysis Peptides Thiourea Thioureas |
| title | Direct N‐Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co‐Catalysis |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-18T21%3A39%3A08IST&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=Direct%20N%E2%80%90Glycofunctionalization%20of%20Amides%20with%20Glycosyl%20Trichloroacetimidate%20by%20Thiourea/Halogen%20Bond%20Donor%20Co%E2%80%90Catalysis&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Kobayashi,%20Yusuke&rft.date=2018-03-26&rft.volume=57&rft.issue=14&rft.spage=3646&rft.epage=3650&rft.pages=3646-3650&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201712726&rft_dat=%3Cproquest_cross%3E1999193792%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=2017712578&rft_id=info:pmid/29412493&rfr_iscdi=true |