Regioselective modification of unprotected glycosides
Selective modification of unprotected carbohydrates is difficult due to the similar reactivity of the hydroxyl groups. In carbohydrate synthesis, therefore, even straightforward transformations often require multiple synthetic steps. The development of selective methods for carbohydrate modification...
Gespeichert in:
| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (4), p.656-664 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 664 |
|---|---|
| container_issue | 4 |
| container_start_page | 656 |
| container_title | Chemical communications (Cambridge, England) |
| container_volume | 52 |
| creator | Jäger, Manuel Minnaard, Adriaan J |
| description | Selective modification of unprotected carbohydrates is difficult due to the similar reactivity of the hydroxyl groups. In carbohydrate synthesis, therefore, even straightforward transformations often require multiple synthetic steps. The development of selective methods for carbohydrate modification is consequently highly desired. This review describes the methods for the regio- and chemoselective carbohydrate modification, with a focus on novel approaches that mainly apply transition metal catalysis and organocatalysis, and discusses the challenges and opportunities in this field.
The regioselective modification of unprotected glycosides represents shortcuts in carbohydrate chemistry and enables efficient routes to complex derivatives. |
| doi_str_mv | 10.1039/c5cc08199h |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1751995253</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1751995253</sourcerecordid><originalsourceid>FETCH-LOGICAL-c485t-52d76e0674f84a169078cba69eac34f81e626b7be629137d5f3a682de16a61003</originalsourceid><addsrcrecordid>eNqFkc1Lw0AQxRdRbK1evCs5ihDdzX7mKEGtUBBEwVvY7E7qStKt2aTQ_96trfXoXN4w8-MxvEHonOAbgml-a7gxWJE8_zhAY0IFSzlT74ebnueppIyP0EkInzgW4eoYjTLBhWJMjhF_gbnzARowvVtB0nrramd07_wi8XUyLJad7-MSbDJv1sYHZyGcoqNaNwHOdjpBbw_3r8U0nT0_PhV3s9QwxfuUZ1YKwEKyWjFNRI6lMpUWOWhD44yAyEQlqyg5odLymmqhMgtEaEEwphN0tfWNR3wNEPqydcFA0-gF-CGURGHMJFEi-x-VPCbEM04jer1FTedD6KAul51rdbcuCS43iZYFL4qfRKcRvtz5DlULdo_-RhiBiy3QBbPf_r2EfgN_Hnmg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1751995253</pqid></control><display><type>article</type><title>Regioselective modification of unprotected glycosides</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals</source><source>Alma/SFX Local Collection</source><creator>Jäger, Manuel ; Minnaard, Adriaan J</creator><creatorcontrib>Jäger, Manuel ; Minnaard, Adriaan J</creatorcontrib><description>Selective modification of unprotected carbohydrates is difficult due to the similar reactivity of the hydroxyl groups. In carbohydrate synthesis, therefore, even straightforward transformations often require multiple synthetic steps. The development of selective methods for carbohydrate modification is consequently highly desired. This review describes the methods for the regio- and chemoselective carbohydrate modification, with a focus on novel approaches that mainly apply transition metal catalysis and organocatalysis, and discusses the challenges and opportunities in this field.
The regioselective modification of unprotected glycosides represents shortcuts in carbohydrate chemistry and enables efficient routes to complex derivatives.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c5cc08199h</identifier><identifier>PMID: 26568447</identifier><language>eng</language><publisher>England</publisher><subject>Carbohydrates ; Carbohydrates - chemical synthesis ; Carbohydrates - chemistry ; Catalysis ; Glycosides ; Glycosides - chemical synthesis ; Glycosides - chemistry ; Glycosylation ; Hydroxyl groups ; Stereoisomerism ; Synthesis ; Transformations ; Transition metals</subject><ispartof>Chemical communications (Cambridge, England), 2016-01, Vol.52 (4), p.656-664</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c485t-52d76e0674f84a169078cba69eac34f81e626b7be629137d5f3a682de16a61003</citedby><cites>FETCH-LOGICAL-c485t-52d76e0674f84a169078cba69eac34f81e626b7be629137d5f3a682de16a61003</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26568447$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jäger, Manuel</creatorcontrib><creatorcontrib>Minnaard, Adriaan J</creatorcontrib><title>Regioselective modification of unprotected glycosides</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Selective modification of unprotected carbohydrates is difficult due to the similar reactivity of the hydroxyl groups. In carbohydrate synthesis, therefore, even straightforward transformations often require multiple synthetic steps. The development of selective methods for carbohydrate modification is consequently highly desired. This review describes the methods for the regio- and chemoselective carbohydrate modification, with a focus on novel approaches that mainly apply transition metal catalysis and organocatalysis, and discusses the challenges and opportunities in this field.
The regioselective modification of unprotected glycosides represents shortcuts in carbohydrate chemistry and enables efficient routes to complex derivatives.</description><subject>Carbohydrates</subject><subject>Carbohydrates - chemical synthesis</subject><subject>Carbohydrates - chemistry</subject><subject>Catalysis</subject><subject>Glycosides</subject><subject>Glycosides - chemical synthesis</subject><subject>Glycosides - chemistry</subject><subject>Glycosylation</subject><subject>Hydroxyl groups</subject><subject>Stereoisomerism</subject><subject>Synthesis</subject><subject>Transformations</subject><subject>Transition metals</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1Lw0AQxRdRbK1evCs5ihDdzX7mKEGtUBBEwVvY7E7qStKt2aTQ_96trfXoXN4w8-MxvEHonOAbgml-a7gxWJE8_zhAY0IFSzlT74ebnueppIyP0EkInzgW4eoYjTLBhWJMjhF_gbnzARowvVtB0nrramd07_wi8XUyLJad7-MSbDJv1sYHZyGcoqNaNwHOdjpBbw_3r8U0nT0_PhV3s9QwxfuUZ1YKwEKyWjFNRI6lMpUWOWhD44yAyEQlqyg5odLymmqhMgtEaEEwphN0tfWNR3wNEPqydcFA0-gF-CGURGHMJFEi-x-VPCbEM04jer1FTedD6KAul51rdbcuCS43iZYFL4qfRKcRvtz5DlULdo_-RhiBiy3QBbPf_r2EfgN_Hnmg</recordid><startdate>20160101</startdate><enddate>20160101</enddate><creator>Jäger, Manuel</creator><creator>Minnaard, Adriaan J</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20160101</creationdate><title>Regioselective modification of unprotected glycosides</title><author>Jäger, Manuel ; Minnaard, Adriaan J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c485t-52d76e0674f84a169078cba69eac34f81e626b7be629137d5f3a682de16a61003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Carbohydrates</topic><topic>Carbohydrates - chemical synthesis</topic><topic>Carbohydrates - chemistry</topic><topic>Catalysis</topic><topic>Glycosides</topic><topic>Glycosides - chemical synthesis</topic><topic>Glycosides - chemistry</topic><topic>Glycosylation</topic><topic>Hydroxyl groups</topic><topic>Stereoisomerism</topic><topic>Synthesis</topic><topic>Transformations</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jäger, Manuel</creatorcontrib><creatorcontrib>Minnaard, Adriaan J</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jäger, Manuel</au><au>Minnaard, Adriaan J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective modification of unprotected glycosides</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2016-01-01</date><risdate>2016</risdate><volume>52</volume><issue>4</issue><spage>656</spage><epage>664</epage><pages>656-664</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Selective modification of unprotected carbohydrates is difficult due to the similar reactivity of the hydroxyl groups. In carbohydrate synthesis, therefore, even straightforward transformations often require multiple synthetic steps. The development of selective methods for carbohydrate modification is consequently highly desired. This review describes the methods for the regio- and chemoselective carbohydrate modification, with a focus on novel approaches that mainly apply transition metal catalysis and organocatalysis, and discusses the challenges and opportunities in this field.
The regioselective modification of unprotected glycosides represents shortcuts in carbohydrate chemistry and enables efficient routes to complex derivatives.</abstract><cop>England</cop><pmid>26568447</pmid><doi>10.1039/c5cc08199h</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2016-01, Vol.52 (4), p.656-664 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1751995253 |
| source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Carbohydrates Carbohydrates - chemical synthesis Carbohydrates - chemistry Catalysis Glycosides Glycosides - chemical synthesis Glycosides - chemistry Glycosylation Hydroxyl groups Stereoisomerism Synthesis Transformations Transition metals |
| title | Regioselective modification of unprotected glycosides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T20%3A35%3A52IST&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=Regioselective%20modification%20of%20unprotected%20glycosides&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=J%C3%A4ger,%20Manuel&rft.date=2016-01-01&rft.volume=52&rft.issue=4&rft.spage=656&rft.epage=664&rft.pages=656-664&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/c5cc08199h&rft_dat=%3Cproquest_cross%3E1751995253%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=1751995253&rft_id=info:pmid/26568447&rfr_iscdi=true |