Mixed‐Electrolyte‐Driven Stereoselective Electrochemical Glycosylation
Mixed electrolytes such as tetrabutylammonium triflate (Bu4NOTf) and tetrabutylammonium bis(trifluoromethanesulfonyl‐amide) (Bu4NNTf2) were found to improve stereoselectivity in electrochemical glycosylation of thioglycosides building blocks without a stereocontrolling group. Bu4NOTf was crucial to...
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| Veröffentlicht in: | ChemElectroChem 2019-08, Vol.6 (16), p.4149-4152 |
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| creator | Isoda, Yuta Kitamura, Kei Takahashi, Shuji Nokami, Toshiki Itoh, Toshiyuki |
| description | Mixed electrolytes such as tetrabutylammonium triflate (Bu4NOTf) and tetrabutylammonium bis(trifluoromethanesulfonyl‐amide) (Bu4NNTf2) were found to improve stereoselectivity in electrochemical glycosylation of thioglycosides building blocks without a stereocontrolling group. Bu4NOTf was crucial to generate glycosyl triflate intermediate, whereas a second electrolyte such as Bu4NNTf2 contributes reducing solution resistance. Therefore, we assume that Bu4NOTf works as a reservoir of the triflate anion of the glycosyl triflate intermediate and Bu4NNTf2 works only as an electrolyte.
A mixed bag: Mixing two different electrolytes enables electrochemical glycosylation in higher stereoselectivity. |
| doi_str_mv | 10.1002/celc.201900215 |
| format | Article |
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A mixed bag: Mixing two different electrolytes enables electrochemical glycosylation in higher stereoselectivity.</description><subject>electrochemical glycosylation</subject><subject>electrolyte</subject><subject>Electrolytes</subject><subject>glycosyl triflate</subject><subject>Stereoselectivity</subject><subject>thioglycoside</subject><issn>2196-0216</issn><issn>2196-0216</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkLFOwzAQhi0EElXpylyJOeXsJE4yohAKqIiB7pZrX0QqNy52CmTjEXhGngRHrYCN6e6_-_476SfknMKMArBLhUbNGNAiCJoekRGjBY9Cz4__9Kdk4v0aACiFNM75iNw_NO-ovz4-K4Oqc9b0HQZ17ZpXbKdPHTq0HoddGEwPkHrGTaOkmc5Nr6zvjewa256Rk1oaj5NDHZPlTbUsb6PF4_yuvFpEKmGQRrksUmBcYbICliLTQeqCK6kzzTKs60wyxYHzVc4SpiGOKRR1nq6Qa5XpeEwu9me3zr7s0HdibXeuDR8FY1kCeQwxD9RsTylnvXdYi61rNtL1goIYEhNDYuInsWAo9oa3xmD_Dy3KalH-er8BPApxzg</recordid><startdate>20190816</startdate><enddate>20190816</enddate><creator>Isoda, Yuta</creator><creator>Kitamura, Kei</creator><creator>Takahashi, Shuji</creator><creator>Nokami, Toshiki</creator><creator>Itoh, Toshiyuki</creator><general>John Wiley & Sons, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0001-5447-4533</orcidid></search><sort><creationdate>20190816</creationdate><title>Mixed‐Electrolyte‐Driven Stereoselective Electrochemical Glycosylation</title><author>Isoda, Yuta ; Kitamura, Kei ; Takahashi, Shuji ; Nokami, Toshiki ; Itoh, Toshiyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4205-8a95026ce4b025e2d950d96cad7d27eff7a2c6066b8242d033109f85be6dc7d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>electrochemical glycosylation</topic><topic>electrolyte</topic><topic>Electrolytes</topic><topic>glycosyl triflate</topic><topic>Stereoselectivity</topic><topic>thioglycoside</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Isoda, Yuta</creatorcontrib><creatorcontrib>Kitamura, Kei</creatorcontrib><creatorcontrib>Takahashi, Shuji</creatorcontrib><creatorcontrib>Nokami, Toshiki</creatorcontrib><creatorcontrib>Itoh, Toshiyuki</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>ChemElectroChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Isoda, Yuta</au><au>Kitamura, Kei</au><au>Takahashi, Shuji</au><au>Nokami, Toshiki</au><au>Itoh, Toshiyuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mixed‐Electrolyte‐Driven Stereoselective Electrochemical Glycosylation</atitle><jtitle>ChemElectroChem</jtitle><date>2019-08-16</date><risdate>2019</risdate><volume>6</volume><issue>16</issue><spage>4149</spage><epage>4152</epage><pages>4149-4152</pages><issn>2196-0216</issn><eissn>2196-0216</eissn><abstract>Mixed electrolytes such as tetrabutylammonium triflate (Bu4NOTf) and tetrabutylammonium bis(trifluoromethanesulfonyl‐amide) (Bu4NNTf2) were found to improve stereoselectivity in electrochemical glycosylation of thioglycosides building blocks without a stereocontrolling group. Bu4NOTf was crucial to generate glycosyl triflate intermediate, whereas a second electrolyte such as Bu4NNTf2 contributes reducing solution resistance. Therefore, we assume that Bu4NOTf works as a reservoir of the triflate anion of the glycosyl triflate intermediate and Bu4NNTf2 works only as an electrolyte.
A mixed bag: Mixing two different electrolytes enables electrochemical glycosylation in higher stereoselectivity.</abstract><cop>Weinheim</cop><pub>John Wiley & Sons, Inc</pub><doi>10.1002/celc.201900215</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-5447-4533</orcidid></addata></record> |
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| language | eng |
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| subjects | electrochemical glycosylation electrolyte Electrolytes glycosyl triflate Stereoselectivity thioglycoside |
| title | Mixed‐Electrolyte‐Driven Stereoselective Electrochemical Glycosylation |
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