Glycosyl 2-Pyridinecarboxylate as an Effective Glycosyl Donor : Glycosidation of Mannose, 2-Azidosugar, and 2-Deoxysugar into Disaccharides
Glycosylation reactions using a glycosyl 2-pyridinecarboxylate as a glycosyl donor were performed. Glycosyl 2-pyridinecarboxylate was designed based on a variation of the Remote Activation Concept and is activated through bidentate coordination to mild Lewis acids such as copper triflate and tin tri...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1998/08/15, Vol.46(8), pp.1244-1247 |
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| container_issue | 8 |
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| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 46 |
| creator | FURUKAWA, Hironori KOIDE, Kazunori TAKAO, Ken-ichi KOBAYASHI, Susumu |
| description | Glycosylation reactions using a glycosyl 2-pyridinecarboxylate as a glycosyl donor were performed. Glycosyl 2-pyridinecarboxylate was designed based on a variation of the Remote Activation Concept and is activated through bidentate coordination to mild Lewis acids such as copper triflate and tin triflate. This method was effective for the glycosidation of not only glucose, but several other sugars such as the mannose-type, 2-azidosugar-type, and 2-deoxysugar-type. Various disaccharides were obtained in excellent yield by this reaction. |
| doi_str_mv | 10.1248/cpb.46.1244 |
| format | Article |
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Glycosyl 2-pyridinecarboxylate was designed based on a variation of the Remote Activation Concept and is activated through bidentate coordination to mild Lewis acids such as copper triflate and tin triflate. This method was effective for the glycosidation of not only glucose, but several other sugars such as the mannose-type, 2-azidosugar-type, and 2-deoxysugar-type. Various disaccharides were obtained in excellent yield by this reaction.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.46.1244</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. 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Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>copper triflate</subject><subject>disaccharide</subject><subject>Exact sciences and technology</subject><subject>glycosyl 2-pyridinecarboxylate</subject><subject>glycosyl donor</subject><subject>glycosylation</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>tin triflate</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><recordid>eNpFkMtOxCAUhonRxPGy8gVYuNMqt5bizjjeEo0udN2cUlBMhQlUY30FX1rqTMYNnPzn4yP5ETqg5IQyUZ_qRXsiqmkWG2hGuZBFyRjfRDNCiCoYr_g22knpjRBWEsln6Oe6H3VIY49Z8ThG1zlvNMQ2fI09DAZDwuDxpbVGD-7T4DU-Dz5EfLYKXAeDCx4Hi-_B-5DMcRaef7supI8XiMfZ0uVkbrL4L8HODwHPXQKtXyF_bNIe2rLQJ7O_unfR89Xl08VNcfdwfXtxfldowcRQWNuREirgnVSlMrRUipZtrdpWcgY174zgUtfK1kJZYNJI1apK2ra1oKmhfBcdLb06hpSisc0iuneIY0NJM_XY5B4bUU2zyPThkl5A0tDbCF67tH7CBBGSVhmbL7G3NMCLWe8hDk73ZlJSVdaTdnVM9v917qAxnv8CeJmNBw</recordid><startdate>1998</startdate><enddate>1998</enddate><creator>FURUKAWA, Hironori</creator><creator>KOIDE, Kazunori</creator><creator>TAKAO, Ken-ichi</creator><creator>KOBAYASHI, Susumu</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>1998</creationdate><title>Glycosyl 2-Pyridinecarboxylate as an Effective Glycosyl Donor : Glycosidation of Mannose, 2-Azidosugar, and 2-Deoxysugar into Disaccharides</title><author>FURUKAWA, Hironori ; KOIDE, Kazunori ; TAKAO, Ken-ichi ; KOBAYASHI, Susumu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c424t-ffd05a6a3d7959e159915b89bb732a83de437c89f849fa27e79b967fbbfac1e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>copper triflate</topic><topic>disaccharide</topic><topic>Exact sciences and technology</topic><topic>glycosyl 2-pyridinecarboxylate</topic><topic>glycosyl donor</topic><topic>glycosylation</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>tin triflate</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>FURUKAWA, Hironori</creatorcontrib><creatorcontrib>KOIDE, Kazunori</creatorcontrib><creatorcontrib>TAKAO, Ken-ichi</creatorcontrib><creatorcontrib>KOBAYASHI, Susumu</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>FURUKAWA, Hironori</au><au>KOIDE, Kazunori</au><au>TAKAO, Ken-ichi</au><au>KOBAYASHI, Susumu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Glycosyl 2-Pyridinecarboxylate as an Effective Glycosyl Donor : Glycosidation of Mannose, 2-Azidosugar, and 2-Deoxysugar into Disaccharides</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1998</date><risdate>1998</risdate><volume>46</volume><issue>8</issue><spage>1244</spage><epage>1247</epage><pages>1244-1247</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Glycosylation reactions using a glycosyl 2-pyridinecarboxylate as a glycosyl donor were performed. Glycosyl 2-pyridinecarboxylate was designed based on a variation of the Remote Activation Concept and is activated through bidentate coordination to mild Lewis acids such as copper triflate and tin triflate. This method was effective for the glycosidation of not only glucose, but several other sugars such as the mannose-type, 2-azidosugar-type, and 2-deoxysugar-type. Various disaccharides were obtained in excellent yield by this reaction.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.46.1244</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1998/08/15, Vol.46(8), pp.1244-1247 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | J-STAGE Free; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry copper triflate disaccharide Exact sciences and technology glycosyl 2-pyridinecarboxylate glycosyl donor glycosylation Organic chemistry Preparations and properties tin triflate |
| title | Glycosyl 2-Pyridinecarboxylate as an Effective Glycosyl Donor : Glycosidation of Mannose, 2-Azidosugar, and 2-Deoxysugar into Disaccharides |
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