Indium-mediated allylation of disaccharides
The indium-mediated allylation followed by ozonolysis has been applied for the elongation of different disaccharides such as cellobiose, lactose and maltose. This reaction sequence and per-O-acetylation produced the expected mixture of α/β-pyranoid as well as α/β-furanoid isomers. The main product i...
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| Veröffentlicht in: | Carbohydrate research 2020-12, Vol.498, p.108170-108170, Article 108170 |
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| container_title | Carbohydrate research |
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| creator | Denner, Christian Gintner, Manuel Kählig, Hanspeter Wrodnigg, Tanja M. Schmid, Walther |
| description | The indium-mediated allylation followed by ozonolysis has been applied for the elongation of different disaccharides such as cellobiose, lactose and maltose. This reaction sequence and per-O-acetylation produced the expected mixture of α/β-pyranoid as well as α/β-furanoid isomers. The main product in all cases adopted the β-pyranose form and could be isolated and fully characterized with the help of NMR-spin simulations. Thorough investigation of the side products throughout optimization of the conditions for the ozonolysis resulted in the discovery of a novel 12 membered bridged disaccharide.
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•Elongation of disaccharides.•Indium-mediated allylation of carbohydrates.•DAISY spin simulation of carbohydrates.•12 Membered bridged bicyclic carbohydrate. |
| doi_str_mv | 10.1016/j.carres.2020.108170 |
| format | Article |
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[Display omitted]
•Elongation of disaccharides.•Indium-mediated allylation of carbohydrates.•DAISY spin simulation of carbohydrates.•12 Membered bridged bicyclic carbohydrate.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2020.108170</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>C–C bond formation ; Disaccharide ; Indium-mediated allylation ; Ozonolysis</subject><ispartof>Carbohydrate research, 2020-12, Vol.498, p.108170-108170, Article 108170</ispartof><rights>2020 The Author(s)</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c385t-587a690d7cfae70c72a94d5ee6782e0d9bb5fbcb41c52830b7d391f8a520219b3</citedby><cites>FETCH-LOGICAL-c385t-587a690d7cfae70c72a94d5ee6782e0d9bb5fbcb41c52830b7d391f8a520219b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.carres.2020.108170$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids></links><search><creatorcontrib>Denner, Christian</creatorcontrib><creatorcontrib>Gintner, Manuel</creatorcontrib><creatorcontrib>Kählig, Hanspeter</creatorcontrib><creatorcontrib>Wrodnigg, Tanja M.</creatorcontrib><creatorcontrib>Schmid, Walther</creatorcontrib><title>Indium-mediated allylation of disaccharides</title><title>Carbohydrate research</title><description>The indium-mediated allylation followed by ozonolysis has been applied for the elongation of different disaccharides such as cellobiose, lactose and maltose. This reaction sequence and per-O-acetylation produced the expected mixture of α/β-pyranoid as well as α/β-furanoid isomers. The main product in all cases adopted the β-pyranose form and could be isolated and fully characterized with the help of NMR-spin simulations. Thorough investigation of the side products throughout optimization of the conditions for the ozonolysis resulted in the discovery of a novel 12 membered bridged disaccharide.
[Display omitted]
•Elongation of disaccharides.•Indium-mediated allylation of carbohydrates.•DAISY spin simulation of carbohydrates.•12 Membered bridged bicyclic carbohydrate.</description><subject>C–C bond formation</subject><subject>Disaccharide</subject><subject>Indium-mediated allylation</subject><subject>Ozonolysis</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LxDAQhoMouK7-Aw89CtJ1kjYfvQiyuLqw4EXBW0iTKab0Y026wv57s9Szh2GY4X1fZh5CbimsKFDx0K6sCQHjigE7rRSVcEYWVMkiL5n4PCcLAFC5YJRfkqsY2zSCkGJB7reD84c-79F5M6HLTNcdOzP5ccjGJnM-Gmu_TPAO4zW5aEwX8eavL8nH5vl9_Zrv3l6266ddbgvFp5wraUQFTtrGoAQrmalKxxGFVAzBVXXNm9rWJbWcqQJq6YqKNsrwdD6t6mJJ7ubcfRi_Dxgn3ftosevMgOMhalZyqlKBSNJyltowxhiw0fvgexOOmoI-sdGtntnoExs9s0m2x9mG6Y0fj0FH63GwCUJAO2k3-v8DfgGDU24P</recordid><startdate>202012</startdate><enddate>202012</enddate><creator>Denner, Christian</creator><creator>Gintner, Manuel</creator><creator>Kählig, Hanspeter</creator><creator>Wrodnigg, Tanja M.</creator><creator>Schmid, Walther</creator><general>Elsevier Ltd</general><scope>6I.</scope><scope>AAFTH</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>202012</creationdate><title>Indium-mediated allylation of disaccharides</title><author>Denner, Christian ; Gintner, Manuel ; Kählig, Hanspeter ; Wrodnigg, Tanja M. ; Schmid, Walther</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c385t-587a690d7cfae70c72a94d5ee6782e0d9bb5fbcb41c52830b7d391f8a520219b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>C–C bond formation</topic><topic>Disaccharide</topic><topic>Indium-mediated allylation</topic><topic>Ozonolysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Denner, Christian</creatorcontrib><creatorcontrib>Gintner, Manuel</creatorcontrib><creatorcontrib>Kählig, Hanspeter</creatorcontrib><creatorcontrib>Wrodnigg, Tanja M.</creatorcontrib><creatorcontrib>Schmid, Walther</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Denner, Christian</au><au>Gintner, Manuel</au><au>Kählig, Hanspeter</au><au>Wrodnigg, Tanja M.</au><au>Schmid, Walther</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Indium-mediated allylation of disaccharides</atitle><jtitle>Carbohydrate research</jtitle><date>2020-12</date><risdate>2020</risdate><volume>498</volume><spage>108170</spage><epage>108170</epage><pages>108170-108170</pages><artnum>108170</artnum><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>The indium-mediated allylation followed by ozonolysis has been applied for the elongation of different disaccharides such as cellobiose, lactose and maltose. This reaction sequence and per-O-acetylation produced the expected mixture of α/β-pyranoid as well as α/β-furanoid isomers. The main product in all cases adopted the β-pyranose form and could be isolated and fully characterized with the help of NMR-spin simulations. Thorough investigation of the side products throughout optimization of the conditions for the ozonolysis resulted in the discovery of a novel 12 membered bridged disaccharide.
[Display omitted]
•Elongation of disaccharides.•Indium-mediated allylation of carbohydrates.•DAISY spin simulation of carbohydrates.•12 Membered bridged bicyclic carbohydrate.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.carres.2020.108170</doi><tpages>1</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Carbohydrate research, 2020-12, Vol.498, p.108170-108170, Article 108170 |
| issn | 0008-6215 1873-426X |
| language | eng |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | C–C bond formation Disaccharide Indium-mediated allylation Ozonolysis |
| title | Indium-mediated allylation of disaccharides |
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