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Conditions for neighboring-group participation in displacement reactions of 5- O-sulfonyl- d-glucofuranose derivatives
Sulfonate displacement reactions of 6- O-benzoyl-1,2- O-isopropylidene-5- O- p-tolylsulfonyl-α- d-glucofuranose derivatives with acetate or chloride ions in acetic anhydride are shown to involve participation by the neighboring benzoyloxy group. Acetate displacement in N,N-dimethylformamide appears...
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| Published in: | Carbohydrate research 1971-11, Vol.20 (1), p.151-164 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c275t-e56a98608749c0e1c37cef6d109ca176138c921111b7d732242f80d7d42b51443 |
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| cites | cdi_FETCH-LOGICAL-c275t-e56a98608749c0e1c37cef6d109ca176138c921111b7d732242f80d7d42b51443 |
| container_end_page | 164 |
| container_issue | 1 |
| container_start_page | 151 |
| container_title | Carbohydrate research |
| container_volume | 20 |
| creator | Chalk, R.C. Ball, D.H. Long, L. |
| description | Sulfonate displacement reactions of 6-
O-benzoyl-1,2-
O-isopropylidene-5-
O-
p-tolylsulfonyl-α-
d-glucofuranose derivatives with acetate or chloride ions in acetic anhydride are shown to involve participation by the neighboring benzoyloxy group. Acetate displacement in
N,N-dimethylformamide appears to occur by both this and the S
n2 mechanism, but, with sodium azide in hexamethylphosphoramide, only the S
n2 displacement product was formed.
Benzylidenation of 1,2-
O-isopropylidene-β-
l-idofuranose gave the 3,5-
O-benzylidene derivative, and the reaction of this acetal with
N-bromosuccinimide gave exclusively 5-
O-benzoyl-6-bromo-6-deoxy-1,2-
O-isopropylidene-β-
l-idofuranose. |
| doi_str_mv | 10.1016/S0008-6215(00)84957-5 |
| format | article |
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O-benzoyl-1,2-
O-isopropylidene-5-
O-
p-tolylsulfonyl-α-
d-glucofuranose derivatives with acetate or chloride ions in acetic anhydride are shown to involve participation by the neighboring benzoyloxy group. Acetate displacement in
N,N-dimethylformamide appears to occur by both this and the S
n2 mechanism, but, with sodium azide in hexamethylphosphoramide, only the S
n2 displacement product was formed.
Benzylidenation of 1,2-
O-isopropylidene-β-
l-idofuranose gave the 3,5-
O-benzylidene derivative, and the reaction of this acetal with
N-bromosuccinimide gave exclusively 5-
O-benzoyl-6-bromo-6-deoxy-1,2-
O-isopropylidene-β-
l-idofuranose.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/S0008-6215(00)84957-5</identifier><identifier>PMID: 5151188</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Acetals ; Acetates ; Anhydrides ; Azides ; Benzoates ; Benzyl Compounds ; Chemical Phenomena ; Chemistry ; Chlorides ; Chromatography, Ion Exchange ; Dimethylformamide ; Furans ; Glucose ; Phosphoric Acids ; Pyrrolidinones ; Sulfonic Acids ; Tosyl Compounds</subject><ispartof>Carbohydrate research, 1971-11, Vol.20 (1), p.151-164</ispartof><rights>1971</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c275t-e56a98608749c0e1c37cef6d109ca176138c921111b7d732242f80d7d42b51443</citedby><cites>FETCH-LOGICAL-c275t-e56a98608749c0e1c37cef6d109ca176138c921111b7d732242f80d7d42b51443</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0008621500849575$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3605,27924,27925,46009</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/5151188$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chalk, R.C.</creatorcontrib><creatorcontrib>Ball, D.H.</creatorcontrib><creatorcontrib>Long, L.</creatorcontrib><title>Conditions for neighboring-group participation in displacement reactions of 5- O-sulfonyl- d-glucofuranose derivatives</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>Sulfonate displacement reactions of 6-
O-benzoyl-1,2-
O-isopropylidene-5-
O-
p-tolylsulfonyl-α-
d-glucofuranose derivatives with acetate or chloride ions in acetic anhydride are shown to involve participation by the neighboring benzoyloxy group. Acetate displacement in
N,N-dimethylformamide appears to occur by both this and the S
n2 mechanism, but, with sodium azide in hexamethylphosphoramide, only the S
n2 displacement product was formed.
Benzylidenation of 1,2-
O-isopropylidene-β-
l-idofuranose gave the 3,5-
O-benzylidene derivative, and the reaction of this acetal with
N-bromosuccinimide gave exclusively 5-
O-benzoyl-6-bromo-6-deoxy-1,2-
O-isopropylidene-β-
l-idofuranose.</description><subject>Acetals</subject><subject>Acetates</subject><subject>Anhydrides</subject><subject>Azides</subject><subject>Benzoates</subject><subject>Benzyl Compounds</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Chlorides</subject><subject>Chromatography, Ion Exchange</subject><subject>Dimethylformamide</subject><subject>Furans</subject><subject>Glucose</subject><subject>Phosphoric Acids</subject><subject>Pyrrolidinones</subject><subject>Sulfonic Acids</subject><subject>Tosyl Compounds</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1971</creationdate><recordtype>article</recordtype><recordid>eNqFkE9r3DAQxUVJSTdpP0JAp5IelGpk649PJSxtEwjk0BZ6E1ppvFXxSq5kL-Tb15tdcs1chmHem8f8CLkCfgMc1OcfnHPDlAB5zfkn03ZSM_mGrMDohrVC_T4jqxfJO3JR699l5Eqrc3IuQQIYsyL7dU4hTjGnSvtcaMK4_bPJJaYt25Y8j3R0ZYo-ju4gojHREOs4OI87TBMt6PzRnXsqGX1kdR76nJ4GRgPbDrPP_VxcyhVpwBL3y5k91vfkbe-Gih9O_ZL8-vb15_qOPTx-v1_fPjAvtJwYSuU6o7jRbec5gm-0x14F4J13oBU0xncCltrooBshWtEbHnRoxUZC2zaX5OPx7ljyvxnrZHexehwGlzDP1RpoRKsAFqE8Cn3JtRbs7VjizpUnC9weeNtn3vYA03Jun3lbufiuTgHzZofhxXUCvOy_HPe4fLmPWGz1EZPHEAv6yYYcX0n4D0XjkN8</recordid><startdate>197111</startdate><enddate>197111</enddate><creator>Chalk, R.C.</creator><creator>Ball, D.H.</creator><creator>Long, L.</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>197111</creationdate><title>Conditions for neighboring-group participation in displacement reactions of 5- O-sulfonyl- d-glucofuranose derivatives</title><author>Chalk, R.C. ; Ball, D.H. ; Long, L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c275t-e56a98608749c0e1c37cef6d109ca176138c921111b7d732242f80d7d42b51443</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1971</creationdate><topic>Acetals</topic><topic>Acetates</topic><topic>Anhydrides</topic><topic>Azides</topic><topic>Benzoates</topic><topic>Benzyl Compounds</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Chlorides</topic><topic>Chromatography, Ion Exchange</topic><topic>Dimethylformamide</topic><topic>Furans</topic><topic>Glucose</topic><topic>Phosphoric Acids</topic><topic>Pyrrolidinones</topic><topic>Sulfonic Acids</topic><topic>Tosyl Compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chalk, R.C.</creatorcontrib><creatorcontrib>Ball, D.H.</creatorcontrib><creatorcontrib>Long, L.</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>Chalk, R.C.</au><au>Ball, D.H.</au><au>Long, L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Conditions for neighboring-group participation in displacement reactions of 5- O-sulfonyl- d-glucofuranose derivatives</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>1971-11</date><risdate>1971</risdate><volume>20</volume><issue>1</issue><spage>151</spage><epage>164</epage><pages>151-164</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>Sulfonate displacement reactions of 6-
O-benzoyl-1,2-
O-isopropylidene-5-
O-
p-tolylsulfonyl-α-
d-glucofuranose derivatives with acetate or chloride ions in acetic anhydride are shown to involve participation by the neighboring benzoyloxy group. Acetate displacement in
N,N-dimethylformamide appears to occur by both this and the S
n2 mechanism, but, with sodium azide in hexamethylphosphoramide, only the S
n2 displacement product was formed.
Benzylidenation of 1,2-
O-isopropylidene-β-
l-idofuranose gave the 3,5-
O-benzylidene derivative, and the reaction of this acetal with
N-bromosuccinimide gave exclusively 5-
O-benzoyl-6-bromo-6-deoxy-1,2-
O-isopropylidene-β-
l-idofuranose.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>5151188</pmid><doi>10.1016/S0008-6215(00)84957-5</doi><tpages>14</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-6215 |
| ispartof | Carbohydrate research, 1971-11, Vol.20 (1), p.151-164 |
| issn | 0008-6215 1873-426X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_81324611 |
| source | Backfile Package - Organic Chemistry (Legacy) [YCO] |
| subjects | Acetals Acetates Anhydrides Azides Benzoates Benzyl Compounds Chemical Phenomena Chemistry Chlorides Chromatography, Ion Exchange Dimethylformamide Furans Glucose Phosphoric Acids Pyrrolidinones Sulfonic Acids Tosyl Compounds |
| title | Conditions for neighboring-group participation in displacement reactions of 5- O-sulfonyl- d-glucofuranose derivatives |
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