Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides

Methyl glycopyranosides reacted with diethylaminosulfur trifluoride (DAST) in the absence of solvent to yield methyl dideoxy-difluoro and deoxy-fluoro glycopyranosides. Methyl α-d-glycopyranosides produced 6-deoxy-6-fluoro- and 4,6-dideoxy-4,6-difluoro derivatives with Walden inversion at C-4. Methy...

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Veröffentlicht in:	Carbohydrate research 1983-09, Vol.121, p.51-60
Hauptverfasser:	Somawardhana, Chandrasiri W., Brunngraber, Eric G.
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemical reactivity Chemistry Diethylamines Exact sciences and technology Fluorine Glycosides Indicators and Reagents Magnetic Resonance Spectroscopy Organic chemistry Reactivity and mechanisms
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container_title	Carbohydrate research
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creator	Somawardhana, Chandrasiri W. Brunngraber, Eric G.
description	Methyl glycopyranosides reacted with diethylaminosulfur trifluoride (DAST) in the absence of solvent to yield methyl dideoxy-difluoro and deoxy-fluoro glycopyranosides. Methyl α-d-glycopyranosides produced 6-deoxy-6-fluoro- and 4,6-dideoxy-4,6-difluoro derivatives with Walden inversion at C-4. Methyl β-d-glucopyranoside also produced a 3,6-dideoxy-3,6-difluoro derivative, with Walden inversion at C-3. Methyl 6-O-trityl-α-d-glucopyranoside, reacted with DAST to yield the corresponding 4-deoxy-4-fluorogalactopyranoside derivative.
doi_str_mv	10.1016/0008-6215(83)84005-1
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Methyl α-d-glycopyranosides produced 6-deoxy-6-fluoro- and 4,6-dideoxy-4,6-difluoro derivatives with Walden inversion at C-4. Methyl β-d-glucopyranoside also produced a 3,6-dideoxy-3,6-difluoro derivative, with Walden inversion at C-3. Methyl 6-O-trityl-α-d-glucopyranoside, reacted with DAST to yield the corresponding 4-deoxy-4-fluorogalactopyranoside derivative.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/0008-6215(83)84005-1</identifier><identifier>PMID: 6667469</identifier><identifier>CODEN: CRBRAT</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Chemical reactivity ; Chemistry ; Diethylamines ; Exact sciences and technology ; Fluorine ; Glycosides ; Indicators and Reagents ; Magnetic Resonance Spectroscopy ; Organic chemistry ; Reactivity and mechanisms</subject><ispartof>Carbohydrate research, 1983-09, Vol.121, p.51-60</ispartof><rights>1983</rights><rights>1984 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c301t-45efc2958854b3540d1467ec22afb249acfa30858862aae2f7b6792cc687480f3</citedby><cites>FETCH-LOGICAL-c301t-45efc2958854b3540d1467ec22afb249acfa30858862aae2f7b6792cc687480f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0008-6215(83)84005-1$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9305405$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6667469$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Somawardhana, Chandrasiri W.</creatorcontrib><creatorcontrib>Brunngraber, Eric G.</creatorcontrib><title>Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>Methyl glycopyranosides reacted with diethylaminosulfur trifluoride (DAST) in the absence of solvent to yield methyl dideoxy-difluoro and deoxy-fluoro glycopyranosides. 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Methyl 6-O-trityl-α-d-glucopyranoside, reacted with DAST to yield the corresponding 4-deoxy-4-fluorogalactopyranoside derivative.</description><subject>Chemical reactivity</subject><subject>Chemistry</subject><subject>Diethylamines</subject><subject>Exact sciences and technology</subject><subject>Fluorine</subject><subject>Glycosides</subject><subject>Indicators and Reagents</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Organic chemistry</subject><subject>Reactivity and mechanisms</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcGKFDEURYMoY8_oHyhkIaKL0iSVpFIbQQZHhQEXKrgLr1MvbSRVGZPUQP-96emml67C4517SU4IecHZO864fs8YM50WXL0x_VsjGVMdf0Q23Ax9J4X-9ZhszshTclnKnzYyPegLcqG1HqQeNyR9r5gxdRSWiWbchdQVjOhquA91T5OnU8D6ex9hDksqa_RrpjUHH9eUw4QUCgV6nBaoYdm1FtjhUqlPmc4PWbqLe5dKw8sz8sRDLPj8dF6Rnzefflx_6W6_ff56_fG2cz3jtZMKvROjMkbJba8km7jUAzohwG-FHMF56Jlpey0AUPhhq4dROKfNIA3z_RV5fey9y-nviqXaORSHMcKCaS3WMDOoUfEGyiPociolo7d3OcyQ95Yze_BsDxLtQaI1vX3wbA-xl6f-dTvjdA6dxLb9q9MeioPoMywulDM29qw9SjXswxHD5uI-YLbFBVwcTiG3T7BTCv-_xz8JiZsk</recordid><startdate>19830916</startdate><enddate>19830916</enddate><creator>Somawardhana, Chandrasiri W.</creator><creator>Brunngraber, Eric G.</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><scope>IQODW</scope><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>19830916</creationdate><title>Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides</title><author>Somawardhana, Chandrasiri W. ; Brunngraber, Eric G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c301t-45efc2958854b3540d1467ec22afb249acfa30858862aae2f7b6792cc687480f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1983</creationdate><topic>Chemical reactivity</topic><topic>Chemistry</topic><topic>Diethylamines</topic><topic>Exact sciences and technology</topic><topic>Fluorine</topic><topic>Glycosides</topic><topic>Indicators and Reagents</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Organic chemistry</topic><topic>Reactivity and mechanisms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Somawardhana, Chandrasiri W.</creatorcontrib><creatorcontrib>Brunngraber, Eric G.</creatorcontrib><collection>Pascal-Francis</collection><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>Somawardhana, Chandrasiri W.</au><au>Brunngraber, Eric G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>1983-09-16</date><risdate>1983</risdate><volume>121</volume><spage>51</spage><epage>60</epage><pages>51-60</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><coden>CRBRAT</coden><abstract>Methyl glycopyranosides reacted with diethylaminosulfur trifluoride (DAST) in the absence of solvent to yield methyl dideoxy-difluoro and deoxy-fluoro glycopyranosides. 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source	MEDLINE; ScienceDirect Journals (5 years ago - present)
subjects	Chemical reactivity Chemistry Diethylamines Exact sciences and technology Fluorine Glycosides Indicators and Reagents Magnetic Resonance Spectroscopy Organic chemistry Reactivity and mechanisms
title	Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides
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