Facile, Efficient, and Enantiospecific Syntheses of 1,1‘-N-Linked Pseudodisaccharides as a New Class of Glycosidase Inhibitors
This article describes an efficient synthesis of a potent trehalase inhibitor, 1,1‘-N-linked pseudodisaccharide 1 (consisting of two valienamines), in 14 steps with an overall yield of 12% and a first synthesis of 2 (consisting of two 2-epi-valienamines) in 15 steps with an overall yield of 24% from...
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| Veröffentlicht in: | Journal of the American Chemical Society 2004-12, Vol.126 (49), p.15990-15992 |
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| container_end_page | 15992 |
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| container_issue | 49 |
| container_start_page | 15990 |
| container_title | Journal of the American Chemical Society |
| container_volume | 126 |
| creator | Shing, Tony K. M Kwong, Connie S. K Cheung, Aries W. C Kok, Stanton H.-L Yu, Zhifeng Li, Jianmei Cheng, Christopher H. K |
| description | This article describes an efficient synthesis of a potent trehalase inhibitor, 1,1‘-N-linked pseudodisaccharide 1 (consisting of two valienamines), in 14 steps with an overall yield of 12% and a first synthesis of 2 (consisting of two 2-epi-valienamines) in 15 steps with an overall yield of 24% from (−)-quinic acid. The synthesis involves a stereospecific palladium-catalyzed coupling reaction between an allylic amine and an allylic chloride as the crucial step. The acetonide blocking groups were shown to be the best hydroxyl protecting groups, compatible with the palladium-catalyzed allylic amination reaction that afforded high yields of the 1,1‘-N-linked pseudodisaccharides with a minimum amount of an elimination diene side product. |
| doi_str_mv | 10.1021/ja0470158 |
| format | Article |
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The acetonide blocking groups were shown to be the best hydroxyl protecting groups, compatible with the palladium-catalyzed allylic amination reaction that afforded high yields of the 1,1‘-N-linked pseudodisaccharides with a minimum amount of an elimination diene side product.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja0470158</identifier><identifier>PMID: 15584732</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Catalysis ; Chemistry ; Disaccharides - chemical synthesis ; Disaccharides - pharmacology ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - pharmacology ; Exact sciences and technology ; Glycoside Hydrolases - antagonists & inhibitors ; Organic chemistry ; Palladium - chemistry ; Preparations and properties ; Stereoisomerism</subject><ispartof>Journal of the American Chemical Society, 2004-12, Vol.126 (49), p.15990-15992</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-a83fd934edb5431969cb1a623a261159b9af6fa9929e05f28b41eeced51295953</citedby><cites>FETCH-LOGICAL-a381t-a83fd934edb5431969cb1a623a261159b9af6fa9929e05f28b41eeced51295953</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja0470158$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja0470158$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27059,27907,27908,56721,56771</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16347306$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15584732$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shing, Tony K. M</creatorcontrib><creatorcontrib>Kwong, Connie S. K</creatorcontrib><creatorcontrib>Cheung, Aries W. C</creatorcontrib><creatorcontrib>Kok, Stanton H.-L</creatorcontrib><creatorcontrib>Yu, Zhifeng</creatorcontrib><creatorcontrib>Li, Jianmei</creatorcontrib><creatorcontrib>Cheng, Christopher H. K</creatorcontrib><title>Facile, Efficient, and Enantiospecific Syntheses of 1,1‘-N-Linked Pseudodisaccharides as a New Class of Glycosidase Inhibitors</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>This article describes an efficient synthesis of a potent trehalase inhibitor, 1,1‘-N-linked pseudodisaccharide 1 (consisting of two valienamines), in 14 steps with an overall yield of 12% and a first synthesis of 2 (consisting of two 2-epi-valienamines) in 15 steps with an overall yield of 24% from (−)-quinic acid. The synthesis involves a stereospecific palladium-catalyzed coupling reaction between an allylic amine and an allylic chloride as the crucial step. The acetonide blocking groups were shown to be the best hydroxyl protecting groups, compatible with the palladium-catalyzed allylic amination reaction that afforded high yields of the 1,1‘-N-linked pseudodisaccharides with a minimum amount of an elimination diene side product.</description><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Disaccharides - chemical synthesis</subject><subject>Disaccharides - pharmacology</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Exact sciences and technology</subject><subject>Glycoside Hydrolases - antagonists & inhibitors</subject><subject>Organic chemistry</subject><subject>Palladium - chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0N9q2zAUBnAzNta028VeYOhmg0G8SbJlW5clpF0hdIV0f9iNOJaPiFLHznRs1tz1MfZ8e5JpS2huBgIhzk8fhy9JXgn-XnApPqyB5yUXqnqSTISSPFVCFk-TCedcpmVVZCfJKdE6PnNZiefJiVCqystMTpKHC7C-xSmbO-etx26YMugaNu-gG3xPW7Q-Dthy1w0rJCTWOyam4vfDr_Q6XfjuDht2Qzg2feMJrF1B8E1kEA-7xp9s1gL9-3XZ7mxPvgFCdtWtfO2HPtCL5JmDlvDl4T5LPl_Mb2cf08Wny6vZ-SKFrBJDClXmGp3l2NQqz4QutK0FFDIDWQihdK3BFQ60lhq5crKqc4FosYlVaKVVdpa83eduQ_9jRBrMxpPFtoUO-5FMUcb-JM8jfLeHNvREAZ3ZBr-BsDOCm791m8e6o319CB3rDTZHeeg3gjcHAGShdQE66-noiiwyXkSX7p2nAe8f5xDu4mJZqcztzdLIWfn929elMl-OuWDJrPsxdLG7_yz4B4YZook</recordid><startdate>20041215</startdate><enddate>20041215</enddate><creator>Shing, Tony K. 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K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-a83fd934edb5431969cb1a623a261159b9af6fa9929e05f28b41eeced51295953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Disaccharides - chemical synthesis</topic><topic>Disaccharides - pharmacology</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Exact sciences and technology</topic><topic>Glycoside Hydrolases - antagonists & inhibitors</topic><topic>Organic chemistry</topic><topic>Palladium - chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shing, Tony K. M</creatorcontrib><creatorcontrib>Kwong, Connie S. K</creatorcontrib><creatorcontrib>Cheung, Aries W. C</creatorcontrib><creatorcontrib>Kok, Stanton H.-L</creatorcontrib><creatorcontrib>Yu, Zhifeng</creatorcontrib><creatorcontrib>Li, Jianmei</creatorcontrib><creatorcontrib>Cheng, Christopher H. 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Chem. Soc</addtitle><date>2004-12-15</date><risdate>2004</risdate><volume>126</volume><issue>49</issue><spage>15990</spage><epage>15992</epage><pages>15990-15992</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>This article describes an efficient synthesis of a potent trehalase inhibitor, 1,1‘-N-linked pseudodisaccharide 1 (consisting of two valienamines), in 14 steps with an overall yield of 12% and a first synthesis of 2 (consisting of two 2-epi-valienamines) in 15 steps with an overall yield of 24% from (−)-quinic acid. The synthesis involves a stereospecific palladium-catalyzed coupling reaction between an allylic amine and an allylic chloride as the crucial step. The acetonide blocking groups were shown to be the best hydroxyl protecting groups, compatible with the palladium-catalyzed allylic amination reaction that afforded high yields of the 1,1‘-N-linked pseudodisaccharides with a minimum amount of an elimination diene side product.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15584732</pmid><doi>10.1021/ja0470158</doi><tpages>3</tpages></addata></record> |
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| subjects | Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Catalysis Chemistry Disaccharides - chemical synthesis Disaccharides - pharmacology Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - pharmacology Exact sciences and technology Glycoside Hydrolases - antagonists & inhibitors Organic chemistry Palladium - chemistry Preparations and properties Stereoisomerism |
| title | Facile, Efficient, and Enantiospecific Syntheses of 1,1‘-N-Linked Pseudodisaccharides as a New Class of Glycosidase Inhibitors |
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