Mild Palladium‐Catalyzed Cyanation of Unprotected 2‐Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2‐Glycoanalogues

Mild Palladium‐Catalyzed Cyanation of Unprotected 2‐Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2‐Glycoanalogues

Access to unprotected 2‐cyano‐glycals via a mild palladium‐catalyzed cyanation of protecting groups‐free 2‐iodoglycals in aqueous media has been developed. Diverse glycal substrates including disaccharide‐type were successfully obtained in good to excellent yields. These unprotected 2‐cyano‐glycal s...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Advanced synthesis & catalysis 2020-03, Vol.362 (5), p.1184-1189
Hauptverfasser: Malinowski, Maciej, Van Tran, Thanh, Robichon, Morgane, Lubin‐Germain, Nadège, Ferry, Angélique
Format: Artikel
Sprache:eng
Schlagworte:
2-iodoglycals
aqueous media
Aqueous solutions
Catalysis
Chemical Sciences
cyanation
Disaccharides
Organic chemistry
Palladium
palladium catalysis
Substrates
unprotected glycosides
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1189
container_issue 5
container_start_page 1184
container_title Advanced synthesis & catalysis
container_volume 362
creator Malinowski, Maciej
Van Tran, Thanh
Robichon, Morgane
Lubin‐Germain, Nadège
Ferry, Angélique
description Access to unprotected 2‐cyano‐glycals via a mild palladium‐catalyzed cyanation of protecting groups‐free 2‐iodoglycals in aqueous media has been developed. Diverse glycal substrates including disaccharide‐type were successfully obtained in good to excellent yields. These unprotected 2‐cyano‐glycal scaffolds were successfully derivatized to different C2‐glycoanalogues.
doi_str_mv 10.1002/adsc.201901583
format Article
fullrecord <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_03553259v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2370311378</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4283-b6b1a9000a53f96e929ff331731e385d17070619fa8e9f172cb835cee760d34d3</originalsourceid><addsrcrecordid>eNqFkb1OwzAUhSMEEr8rsyUmhpZ74zqOxyj8VSoCicJqubYDQaaGOCkKEw_AwDPyJLgqKiOTLd_vnHuvT5IcIgwRID1RJuhhCigAWU43kh3MkA1GmInN9Z3BdrIbwhMA8pzzneTzqnaG3CjnlKm75--Pr1K1yvXv1pCyV3PV1n5OfEXu5i-Nb61uYyGN2Ngb_-B6rVwg9ZwUr531XSBX1tSKqEDubROi2Fky9d6R1pNCaxsCOa0XsWRJuXS5iA4-dnH-obNhP9mqop89-D33krvzs2l5OZhcX4zLYjLQozSng1k2QyUAQDFaicyKVFQVpcgpWpozgxw4ZCgqlVtRIU_1LKdMW8szMHRk6F5yvPJ9VE6-NPWzanrpVS0vi4lcvgFljKZMLDCyRys2rh93DK188l0TJw4ypRwoIuV5pIYrSjc-hMZWa1sEuUxHLtOR63SiQKwEb_GL-n9oWZzeln_aHzQqlkk</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2370311378</pqid></control><display><type>article</type><title>Mild Palladium‐Catalyzed Cyanation of Unprotected 2‐Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2‐Glycoanalogues</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Malinowski, Maciej ; Van Tran, Thanh ; Robichon, Morgane ; Lubin‐Germain, Nadège ; Ferry, Angélique</creator><creatorcontrib>Malinowski, Maciej ; Van Tran, Thanh ; Robichon, Morgane ; Lubin‐Germain, Nadège ; Ferry, Angélique</creatorcontrib><description>Access to unprotected 2‐cyano‐glycals via a mild palladium‐catalyzed cyanation of protecting groups‐free 2‐iodoglycals in aqueous media has been developed. Diverse glycal substrates including disaccharide‐type were successfully obtained in good to excellent yields. These unprotected 2‐cyano‐glycal scaffolds were successfully derivatized to different C2‐glycoanalogues.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201901583</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>2-iodoglycals ; aqueous media ; Aqueous solutions ; Catalysis ; Chemical Sciences ; cyanation ; Disaccharides ; Organic chemistry ; Palladium ; palladium catalysis ; Substrates ; unprotected glycosides</subject><ispartof>Advanced synthesis &amp; catalysis, 2020-03, Vol.362 (5), p.1184-1189</ispartof><rights>2020 Wiley‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4283-b6b1a9000a53f96e929ff331731e385d17070619fa8e9f172cb835cee760d34d3</citedby><cites>FETCH-LOGICAL-c4283-b6b1a9000a53f96e929ff331731e385d17070619fa8e9f172cb835cee760d34d3</cites><orcidid>0000-0002-4586-8482</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%2Fadsc.201901583$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201901583$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,776,780,881,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://hal.science/hal-03553259$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Malinowski, Maciej</creatorcontrib><creatorcontrib>Van Tran, Thanh</creatorcontrib><creatorcontrib>Robichon, Morgane</creatorcontrib><creatorcontrib>Lubin‐Germain, Nadège</creatorcontrib><creatorcontrib>Ferry, Angélique</creatorcontrib><title>Mild Palladium‐Catalyzed Cyanation of Unprotected 2‐Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2‐Glycoanalogues</title><title>Advanced synthesis &amp; catalysis</title><description>Access to unprotected 2‐cyano‐glycals via a mild palladium‐catalyzed cyanation of protecting groups‐free 2‐iodoglycals in aqueous media has been developed. Diverse glycal substrates including disaccharide‐type were successfully obtained in good to excellent yields. These unprotected 2‐cyano‐glycal scaffolds were successfully derivatized to different C2‐glycoanalogues.</description><subject>2-iodoglycals</subject><subject>aqueous media</subject><subject>Aqueous solutions</subject><subject>Catalysis</subject><subject>Chemical Sciences</subject><subject>cyanation</subject><subject>Disaccharides</subject><subject>Organic chemistry</subject><subject>Palladium</subject><subject>palladium catalysis</subject><subject>Substrates</subject><subject>unprotected glycosides</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkb1OwzAUhSMEEr8rsyUmhpZ74zqOxyj8VSoCicJqubYDQaaGOCkKEw_AwDPyJLgqKiOTLd_vnHuvT5IcIgwRID1RJuhhCigAWU43kh3MkA1GmInN9Z3BdrIbwhMA8pzzneTzqnaG3CjnlKm75--Pr1K1yvXv1pCyV3PV1n5OfEXu5i-Nb61uYyGN2Ngb_-B6rVwg9ZwUr531XSBX1tSKqEDubROi2Fky9d6R1pNCaxsCOa0XsWRJuXS5iA4-dnH-obNhP9mqop89-D33krvzs2l5OZhcX4zLYjLQozSng1k2QyUAQDFaicyKVFQVpcgpWpozgxw4ZCgqlVtRIU_1LKdMW8szMHRk6F5yvPJ9VE6-NPWzanrpVS0vi4lcvgFljKZMLDCyRys2rh93DK188l0TJw4ypRwoIuV5pIYrSjc-hMZWa1sEuUxHLtOR63SiQKwEb_GL-n9oWZzeln_aHzQqlkk</recordid><startdate>20200304</startdate><enddate>20200304</enddate><creator>Malinowski, Maciej</creator><creator>Van Tran, Thanh</creator><creator>Robichon, Morgane</creator><creator>Lubin‐Germain, Nadège</creator><creator>Ferry, Angélique</creator><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-4586-8482</orcidid></search><sort><creationdate>20200304</creationdate><title>Mild Palladium‐Catalyzed Cyanation of Unprotected 2‐Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2‐Glycoanalogues</title><author>Malinowski, Maciej ; Van Tran, Thanh ; Robichon, Morgane ; Lubin‐Germain, Nadège ; Ferry, Angélique</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4283-b6b1a9000a53f96e929ff331731e385d17070619fa8e9f172cb835cee760d34d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>2-iodoglycals</topic><topic>aqueous media</topic><topic>Aqueous solutions</topic><topic>Catalysis</topic><topic>Chemical Sciences</topic><topic>cyanation</topic><topic>Disaccharides</topic><topic>Organic chemistry</topic><topic>Palladium</topic><topic>palladium catalysis</topic><topic>Substrates</topic><topic>unprotected glycosides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Malinowski, Maciej</creatorcontrib><creatorcontrib>Van Tran, Thanh</creatorcontrib><creatorcontrib>Robichon, Morgane</creatorcontrib><creatorcontrib>Lubin‐Germain, Nadège</creatorcontrib><creatorcontrib>Ferry, Angélique</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Advanced synthesis &amp; catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Malinowski, Maciej</au><au>Van Tran, Thanh</au><au>Robichon, Morgane</au><au>Lubin‐Germain, Nadège</au><au>Ferry, Angélique</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mild Palladium‐Catalyzed Cyanation of Unprotected 2‐Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2‐Glycoanalogues</atitle><jtitle>Advanced synthesis &amp; catalysis</jtitle><date>2020-03-04</date><risdate>2020</risdate><volume>362</volume><issue>5</issue><spage>1184</spage><epage>1189</epage><pages>1184-1189</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Access to unprotected 2‐cyano‐glycals via a mild palladium‐catalyzed cyanation of protecting groups‐free 2‐iodoglycals in aqueous media has been developed. Diverse glycal substrates including disaccharide‐type were successfully obtained in good to excellent yields. These unprotected 2‐cyano‐glycal scaffolds were successfully derivatized to different C2‐glycoanalogues.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201901583</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-4586-8482</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1615-4150
ispartof Advanced synthesis & catalysis, 2020-03, Vol.362 (5), p.1184-1189
issn 1615-4150
1615-4169
language eng
recordid cdi_hal_primary_oai_HAL_hal_03553259v1
source Wiley Online Library Journals Frontfile Complete
subjects 2-iodoglycals
aqueous media
Aqueous solutions
Catalysis
Chemical Sciences
cyanation
Disaccharides
Organic chemistry
Palladium
palladium catalysis
Substrates
unprotected glycosides
title Mild Palladium‐Catalyzed Cyanation of Unprotected 2‐Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2‐Glycoanalogues
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T14%3A59%3A46IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Mild%20Palladium%E2%80%90Catalyzed%20Cyanation%20of%20Unprotected%202%E2%80%90Iodoglycals%20in%20Aqueous%20Media%20as%20Versatile%20Tool%20to%20Access%20Diverse%20C2%E2%80%90Glycoanalogues&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Malinowski,%20Maciej&rft.date=2020-03-04&rft.volume=362&rft.issue=5&rft.spage=1184&rft.epage=1189&rft.pages=1184-1189&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201901583&rft_dat=%3Cproquest_hal_p%3E2370311378%3C/proquest_hal_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2370311378&rft_id=info:pmid/&rfr_iscdi=true