Solid-supported reagents composed of a copolymer possessing 2-O-sulfonyl mannosides and phase-transfer catalysts for the synthesis of 2-fluoroglucose
[Display omitted] We described the synthesis of a solid-supported co-polymer possessing mannosides and phase-transfer catalysts and synthesis of 2-fluoroglucoside from it. We first prepared a soluble copolymer from two allene monomers possessing a precursor for the synthesis of 2-fluoroglycose and a...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2015-12, Vol.25 (23), p.5500-5503 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Takeuchi, Ryota Sakai, Yuki Tanaka, Hiroshi Takahashi, Takashi |
| description | [Display omitted]
We described the synthesis of a solid-supported co-polymer possessing mannosides and phase-transfer catalysts and synthesis of 2-fluoroglucoside from it. We first prepared a soluble copolymer from two allene monomers possessing a precursor for the synthesis of 2-fluoroglycose and a crown ether. The copolymerization of the monomers via the π-ally nickel-catalyst smoothly proceeded at room temperature to provide a desired copolymer without decomposition of the sulfonate esters. The copolymer exhibited high reactivity towards fluorination in comparison with a conventional precursor. We next synthesized the solid-supported copolymer by using the solid-supported initiator attached with TentaGel® resins. TentaGel® enabled polymerization under stirring with stirring bar without decomposition. The solid-supported copolymer exhibited comparable reactivity towards fluorination in comparison with the soluble copolymer. In addition, it can be easily separated from the reaction vessel by filtration. |
| doi_str_mv | 10.1016/j.bmcl.2015.10.068 |
| format | Article |
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We described the synthesis of a solid-supported co-polymer possessing mannosides and phase-transfer catalysts and synthesis of 2-fluoroglucoside from it. We first prepared a soluble copolymer from two allene monomers possessing a precursor for the synthesis of 2-fluoroglycose and a crown ether. The copolymerization of the monomers via the π-ally nickel-catalyst smoothly proceeded at room temperature to provide a desired copolymer without decomposition of the sulfonate esters. The copolymer exhibited high reactivity towards fluorination in comparison with a conventional precursor. We next synthesized the solid-supported copolymer by using the solid-supported initiator attached with TentaGel® resins. TentaGel® enabled polymerization under stirring with stirring bar without decomposition. The solid-supported copolymer exhibited comparable reactivity towards fluorination in comparison with the soluble copolymer. In addition, it can be easily separated from the reaction vessel by filtration.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2015.10.068</identifier><identifier>PMID: 26525864</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Catalysis ; Fluorination ; Glucose ; Glucose - analogs & derivatives ; Glucose - chemical synthesis ; Glucose - chemistry ; Glucosides - chemical synthesis ; Halogenation ; Mannosides - chemistry ; Molecular Structure ; Phase Transition ; Polymers - chemistry ; Positron emission tomography ; Solid-Phase Synthesis Techniques ; Solid-supported reagents ; Sulfinic Acids - chemistry ; Sulfonate linker</subject><ispartof>Bioorganic & medicinal chemistry letters, 2015-12, Vol.25 (23), p.5500-5503</ispartof><rights>2015 Elsevier Ltd</rights><rights>Copyright © 2015 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c466t-937eefc834a40d1fe9ec4bfecc8c1dc663baa951de5e3ac63e59469120eecc373</citedby><cites>FETCH-LOGICAL-c466t-937eefc834a40d1fe9ec4bfecc8c1dc663baa951de5e3ac63e59469120eecc373</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X15301773$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26525864$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Takeuchi, Ryota</creatorcontrib><creatorcontrib>Sakai, Yuki</creatorcontrib><creatorcontrib>Tanaka, Hiroshi</creatorcontrib><creatorcontrib>Takahashi, Takashi</creatorcontrib><title>Solid-supported reagents composed of a copolymer possessing 2-O-sulfonyl mannosides and phase-transfer catalysts for the synthesis of 2-fluoroglucose</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
We described the synthesis of a solid-supported co-polymer possessing mannosides and phase-transfer catalysts and synthesis of 2-fluoroglucoside from it. We first prepared a soluble copolymer from two allene monomers possessing a precursor for the synthesis of 2-fluoroglycose and a crown ether. The copolymerization of the monomers via the π-ally nickel-catalyst smoothly proceeded at room temperature to provide a desired copolymer without decomposition of the sulfonate esters. The copolymer exhibited high reactivity towards fluorination in comparison with a conventional precursor. We next synthesized the solid-supported copolymer by using the solid-supported initiator attached with TentaGel® resins. TentaGel® enabled polymerization under stirring with stirring bar without decomposition. The solid-supported copolymer exhibited comparable reactivity towards fluorination in comparison with the soluble copolymer. In addition, it can be easily separated from the reaction vessel by filtration.</description><subject>Catalysis</subject><subject>Fluorination</subject><subject>Glucose</subject><subject>Glucose - analogs & derivatives</subject><subject>Glucose - chemical synthesis</subject><subject>Glucose - chemistry</subject><subject>Glucosides - chemical synthesis</subject><subject>Halogenation</subject><subject>Mannosides - chemistry</subject><subject>Molecular Structure</subject><subject>Phase Transition</subject><subject>Polymers - chemistry</subject><subject>Positron emission tomography</subject><subject>Solid-Phase Synthesis Techniques</subject><subject>Solid-supported reagents</subject><subject>Sulfinic Acids - chemistry</subject><subject>Sulfonate linker</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUFr3DAQhUVoSTbb_IEcio69eCvZstaGXkpI20Agh7bQm9BKo40WWXI1dsE_pP-3Mpv22NOgx3vfoHmE3HK244zL96fdYTBhVzPeFmHHZHdBNlxIUTWCta_IhvWSVV0vflyRa8QTY1wwIS7JVS3buu2k2JDfX1PwtsJ5HFOewNIM-ghxQmrSMCYsSnJUl9eYwjJApkVEQPTxSOvqqSSDS3EJdNAxJvQWkOpo6fisEaop64iupIyedFiwcF3KdHoGikssAz2uC-rKhTnldAyzKUvfkNdOB4Sbl7kl3z_df7v7Uj0-fX64-_hYGSHlVPXNHsCZrhFaMMsd9GDEwYExneHWSNkctO5bbqGFRhvZQNsL2fOaQfE0-2ZL3p25Y04_Z8BJDR4NhKAjpBkV3zd83_OukLakPltNLgfI4NSY_aDzojhTax3qpNY61FrHqpU6SujtC38-DGD_Rf7evxg-nA1QfvnLQ1ZoPEQD1mcwk7LJ_4__B-4boPA</recordid><startdate>20151201</startdate><enddate>20151201</enddate><creator>Takeuchi, Ryota</creator><creator>Sakai, Yuki</creator><creator>Tanaka, Hiroshi</creator><creator>Takahashi, Takashi</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>20151201</creationdate><title>Solid-supported reagents composed of a copolymer possessing 2-O-sulfonyl mannosides and phase-transfer catalysts for the synthesis of 2-fluoroglucose</title><author>Takeuchi, Ryota ; Sakai, Yuki ; Tanaka, Hiroshi ; Takahashi, Takashi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c466t-937eefc834a40d1fe9ec4bfecc8c1dc663baa951de5e3ac63e59469120eecc373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Catalysis</topic><topic>Fluorination</topic><topic>Glucose</topic><topic>Glucose - analogs & derivatives</topic><topic>Glucose - chemical synthesis</topic><topic>Glucose - chemistry</topic><topic>Glucosides - chemical synthesis</topic><topic>Halogenation</topic><topic>Mannosides - chemistry</topic><topic>Molecular Structure</topic><topic>Phase Transition</topic><topic>Polymers - chemistry</topic><topic>Positron emission tomography</topic><topic>Solid-Phase Synthesis Techniques</topic><topic>Solid-supported reagents</topic><topic>Sulfinic Acids - chemistry</topic><topic>Sulfonate linker</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Takeuchi, Ryota</creatorcontrib><creatorcontrib>Sakai, Yuki</creatorcontrib><creatorcontrib>Tanaka, Hiroshi</creatorcontrib><creatorcontrib>Takahashi, Takashi</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Takeuchi, Ryota</au><au>Sakai, Yuki</au><au>Tanaka, Hiroshi</au><au>Takahashi, Takashi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solid-supported reagents composed of a copolymer possessing 2-O-sulfonyl mannosides and phase-transfer catalysts for the synthesis of 2-fluoroglucose</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2015-12-01</date><risdate>2015</risdate><volume>25</volume><issue>23</issue><spage>5500</spage><epage>5503</epage><pages>5500-5503</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
We described the synthesis of a solid-supported co-polymer possessing mannosides and phase-transfer catalysts and synthesis of 2-fluoroglucoside from it. We first prepared a soluble copolymer from two allene monomers possessing a precursor for the synthesis of 2-fluoroglycose and a crown ether. The copolymerization of the monomers via the π-ally nickel-catalyst smoothly proceeded at room temperature to provide a desired copolymer without decomposition of the sulfonate esters. The copolymer exhibited high reactivity towards fluorination in comparison with a conventional precursor. We next synthesized the solid-supported copolymer by using the solid-supported initiator attached with TentaGel® resins. TentaGel® enabled polymerization under stirring with stirring bar without decomposition. The solid-supported copolymer exhibited comparable reactivity towards fluorination in comparison with the soluble copolymer. In addition, it can be easily separated from the reaction vessel by filtration.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>26525864</pmid><doi>10.1016/j.bmcl.2015.10.068</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2015-12, Vol.25 (23), p.5500-5503 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Catalysis Fluorination Glucose Glucose - analogs & derivatives Glucose - chemical synthesis Glucose - chemistry Glucosides - chemical synthesis Halogenation Mannosides - chemistry Molecular Structure Phase Transition Polymers - chemistry Positron emission tomography Solid-Phase Synthesis Techniques Solid-supported reagents Sulfinic Acids - chemistry Sulfonate linker |
| title | Solid-supported reagents composed of a copolymer possessing 2-O-sulfonyl mannosides and phase-transfer catalysts for the synthesis of 2-fluoroglucose |
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