Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates
[Display omitted] ► Xtalfluor-E and -M convert thio-, seleno-, and telluroglycosides to glycosyl fluorides. ► Reaction occurs readily without need for additional NBS. ► Sulfoxides are also converted to glycosyl fluorides. ► Mechanistic support delivery of fluoride from tetrafluoroborate counterion....
Gespeichert in:
| Veröffentlicht in: | Carbohydrate research 2012-08, Vol.357, p.16-22 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 22 |
|---|---|
| container_issue | |
| container_start_page | 16 |
| container_title | Carbohydrate research |
| container_volume | 357 |
| creator | Tsegay, Sammi Williams, Rohan J. Williams, Spencer J. |
| description | [Display omitted]
► Xtalfluor-E and -M convert thio-, seleno-, and telluroglycosides to glycosyl fluorides. ► Reaction occurs readily without need for additional NBS. ► Sulfoxides are also converted to glycosyl fluorides. ► Mechanistic support delivery of fluoride from tetrafluoroborate counterion.
Glycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide. Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion. |
| doi_str_mv | 10.1016/j.carres.2012.04.016 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1024933473</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0008621512001929</els_id><sourcerecordid>1024933473</sourcerecordid><originalsourceid>FETCH-LOGICAL-c428t-b9d2a61bb6cce2362e918d71440741c66d5548522e4037ee8fd6961dd827e7f83</originalsourceid><addsrcrecordid>eNp9kcFu3CAQhlHUqLvZ9A2iysceagcwi9lLpWrVNpUi5ZBWyg1hGGdZ2SZl7Cj7Gnni4HWSY0_Azzf_MPyEXDBaMMrk5b6wJkbAglPGCyqKJJ6QJVNVmQsu7z6QJaVU5ZKz9YKcIe7TkcpKfiQLzqXiJWNL8nx76IcdoMcsNNl9e7ABD23WtGOI3gFmTQxdNux8yL9mCC3008b0LhugbccY5pIjOqnvDji2TXg66iP6_j4zne-D80fnMN363o_JGoZoZrEO0QyA5-S0MS3Cp9d1Rf7-_PFne5Vf3_z6vf1-nVvB1ZDXG8eNZHUtrQVeSg4bplzFhKCVYFZKt14LteYcBC0rANU4uZHMOcUrqBpVrsiX2fchhn8j4KA7jzZNZXoII2pGudiUpajKhIoZtenpGKHRD9F3Jh4SpKc09F7PaegpDU2FTmIq-_zaYaw7cO9Fb9-fgG8zAGnORw9Ro_XQW3A-gh20C_7_HV4AAYyhxA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1024933473</pqid></control><display><type>article</type><title>Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals Complete</source><creator>Tsegay, Sammi ; Williams, Rohan J. ; Williams, Spencer J.</creator><creatorcontrib>Tsegay, Sammi ; Williams, Rohan J. ; Williams, Spencer J.</creatorcontrib><description>[Display omitted]
► Xtalfluor-E and -M convert thio-, seleno-, and telluroglycosides to glycosyl fluorides. ► Reaction occurs readily without need for additional NBS. ► Sulfoxides are also converted to glycosyl fluorides. ► Mechanistic support delivery of fluoride from tetrafluoroborate counterion.
Glycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide. Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2012.04.016</identifier><identifier>PMID: 22682311</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Ethylene Dichlorides - chemistry ; Fluorination ; Fluorosugars ; Glycosides - chemical synthesis ; Halogenation ; Hydrocarbons, Fluorinated - chemical synthesis ; Hydrocarbons, Fluorinated - chemistry ; Organometallic Compounds - chemistry ; Organoselenium Compounds - chemistry ; Selenoglycoside ; Solvents - chemistry ; Sulfoxides - chemistry ; Sulfur Compounds - chemistry ; Tellurium - chemistry ; Thioglycoside ; Thioglycosides - chemistry</subject><ispartof>Carbohydrate research, 2012-08, Vol.357, p.16-22</ispartof><rights>2012 Elsevier Ltd</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c428t-b9d2a61bb6cce2362e918d71440741c66d5548522e4037ee8fd6961dd827e7f83</citedby><cites>FETCH-LOGICAL-c428t-b9d2a61bb6cce2362e918d71440741c66d5548522e4037ee8fd6961dd827e7f83</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.2012.04.016$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22682311$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tsegay, Sammi</creatorcontrib><creatorcontrib>Williams, Rohan J.</creatorcontrib><creatorcontrib>Williams, Spencer J.</creatorcontrib><title>Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>[Display omitted]
► Xtalfluor-E and -M convert thio-, seleno-, and telluroglycosides to glycosyl fluorides. ► Reaction occurs readily without need for additional NBS. ► Sulfoxides are also converted to glycosyl fluorides. ► Mechanistic support delivery of fluoride from tetrafluoroborate counterion.
Glycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide. Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion.</description><subject>Ethylene Dichlorides - chemistry</subject><subject>Fluorination</subject><subject>Fluorosugars</subject><subject>Glycosides - chemical synthesis</subject><subject>Halogenation</subject><subject>Hydrocarbons, Fluorinated - chemical synthesis</subject><subject>Hydrocarbons, Fluorinated - chemistry</subject><subject>Organometallic Compounds - chemistry</subject><subject>Organoselenium Compounds - chemistry</subject><subject>Selenoglycoside</subject><subject>Solvents - chemistry</subject><subject>Sulfoxides - chemistry</subject><subject>Sulfur Compounds - chemistry</subject><subject>Tellurium - chemistry</subject><subject>Thioglycoside</subject><subject>Thioglycosides - chemistry</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcFu3CAQhlHUqLvZ9A2iysceagcwi9lLpWrVNpUi5ZBWyg1hGGdZ2SZl7Cj7Gnni4HWSY0_Azzf_MPyEXDBaMMrk5b6wJkbAglPGCyqKJJ6QJVNVmQsu7z6QJaVU5ZKz9YKcIe7TkcpKfiQLzqXiJWNL8nx76IcdoMcsNNl9e7ABD23WtGOI3gFmTQxdNux8yL9mCC3008b0LhugbccY5pIjOqnvDji2TXg66iP6_j4zne-D80fnMN363o_JGoZoZrEO0QyA5-S0MS3Cp9d1Rf7-_PFne5Vf3_z6vf1-nVvB1ZDXG8eNZHUtrQVeSg4bplzFhKCVYFZKt14LteYcBC0rANU4uZHMOcUrqBpVrsiX2fchhn8j4KA7jzZNZXoII2pGudiUpajKhIoZtenpGKHRD9F3Jh4SpKc09F7PaegpDU2FTmIq-_zaYaw7cO9Fb9-fgG8zAGnORw9Ro_XQW3A-gh20C_7_HV4AAYyhxA</recordid><startdate>20120801</startdate><enddate>20120801</enddate><creator>Tsegay, Sammi</creator><creator>Williams, Rohan J.</creator><creator>Williams, Spencer J.</creator><general>Elsevier Ltd</general><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></search><sort><creationdate>20120801</creationdate><title>Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates</title><author>Tsegay, Sammi ; Williams, Rohan J. ; Williams, Spencer J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c428t-b9d2a61bb6cce2362e918d71440741c66d5548522e4037ee8fd6961dd827e7f83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Ethylene Dichlorides - chemistry</topic><topic>Fluorination</topic><topic>Fluorosugars</topic><topic>Glycosides - chemical synthesis</topic><topic>Halogenation</topic><topic>Hydrocarbons, Fluorinated - chemical synthesis</topic><topic>Hydrocarbons, Fluorinated - chemistry</topic><topic>Organometallic Compounds - chemistry</topic><topic>Organoselenium Compounds - chemistry</topic><topic>Selenoglycoside</topic><topic>Solvents - chemistry</topic><topic>Sulfoxides - chemistry</topic><topic>Sulfur Compounds - chemistry</topic><topic>Tellurium - chemistry</topic><topic>Thioglycoside</topic><topic>Thioglycosides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tsegay, Sammi</creatorcontrib><creatorcontrib>Williams, Rohan J.</creatorcontrib><creatorcontrib>Williams, Spencer 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><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tsegay, Sammi</au><au>Williams, Rohan J.</au><au>Williams, Spencer J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2012-08-01</date><risdate>2012</risdate><volume>357</volume><spage>16</spage><epage>22</epage><pages>16-22</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>[Display omitted]
► Xtalfluor-E and -M convert thio-, seleno-, and telluroglycosides to glycosyl fluorides. ► Reaction occurs readily without need for additional NBS. ► Sulfoxides are also converted to glycosyl fluorides. ► Mechanistic support delivery of fluoride from tetrafluoroborate counterion.
Glycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide. Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>22682311</pmid><doi>10.1016/j.carres.2012.04.016</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-6215 |
| ispartof | Carbohydrate research, 2012-08, Vol.357, p.16-22 |
| issn | 0008-6215 1873-426X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1024933473 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Ethylene Dichlorides - chemistry Fluorination Fluorosugars Glycosides - chemical synthesis Halogenation Hydrocarbons, Fluorinated - chemical synthesis Hydrocarbons, Fluorinated - chemistry Organometallic Compounds - chemistry Organoselenium Compounds - chemistry Selenoglycoside Solvents - chemistry Sulfoxides - chemistry Sulfur Compounds - chemistry Tellurium - chemistry Thioglycoside Thioglycosides - chemistry |
| title | Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T09%3A25%3A03IST&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=Synthesis%20of%20glycosyl%20fluorides%20from%20thio-,%20seleno-,%20and%20telluroglycosides%20and%20glycosyl%20sulfoxides%20using%20aminodifluorosulfinium%20tetrafluoroborates&rft.jtitle=Carbohydrate%20research&rft.au=Tsegay,%20Sammi&rft.date=2012-08-01&rft.volume=357&rft.spage=16&rft.epage=22&rft.pages=16-22&rft.issn=0008-6215&rft.eissn=1873-426X&rft_id=info:doi/10.1016/j.carres.2012.04.016&rft_dat=%3Cproquest_cross%3E1024933473%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=1024933473&rft_id=info:pmid/22682311&rft_els_id=S0008621512001929&rfr_iscdi=true |