Matches in SemOpenAlex for { <https://semopenalex.org/work/W2035226246> ?p ?o ?g. }
- W2035226246 endingPage "2676" @default.
- W2035226246 startingPage "2665" @default.
- W2035226246 abstract "C-Glycosidation is of great significance in the organic synthesis of optically active materials, since it allows the introduction of carbon chains to sugar chirons and the use of sugar nuclei as a chiral pool as well as a carbon source. Silylacetylenes are sufficiently reactive to form ‘sugar acetylenes’ for the selective introduction of various acetylenic groups in an alpha-axial manner at the anomeric position of D-hexopyranose rings. 1,4-Anti induction, on the other hand, gives a different stereochemical outcome in the case of C-glycosidation of pentopyranose glycals. The mechanism of these reactions includes oxonium cation intermediates in which stereoelectronic and/or steric factors drive the direction of the incoming silylacetylene. Bis-C-glycosidation allows the introduction of sugars at both ends of some bis(trimethylsilyl)acetylenes. A 2,3-dideoxyglucose derivative provides the corresponding C-1 α-acetylenic compounds, which would increase the scope of C-glycosidation with silylacetylenes. In sugar acetylenes, the alkynyl group at the anomeric position of a pyranose ring is epimerized via a hexacarbonyldicobalt complex by treatment with trifluoromethanesulfonic acid. The three steps—cobalt complexation, acidic transformation and decomplexation—afford overall epimerization and thus one can obtain either the α- or β-alkynyl C-glycoside as desired. Ring opening of a dihydropyran derivative using Nicholas-type cation intermediates is also part of this study. Several sets of decomplexation conditions for endo-type acetylene–cobalt complexes provide various olefins possessing potential utility for synthesis. These methodologies have been utilized for the synthesis of polyoxygenated natural products and derivatives." @default.
- W2035226246 created "2016-06-24" @default.
- W2035226246 creator A5002845487 @default.
- W2035226246 creator A5004486443 @default.
- W2035226246 creator A5016225060 @default.
- W2035226246 creator A5019042345 @default.
- W2035226246 date "1998-01-01" @default.
- W2035226246 modified "2023-10-03" @default.
- W2035226246 title "Stereocontrolled synthesis and reactivity of sugar acetylenes" @default.
- W2035226246 cites W1968114053 @default.
- W2035226246 cites W1971434179 @default.
- W2035226246 cites W1973753517 @default.
- W2035226246 cites W1980967391 @default.
- W2035226246 cites W1995505121 @default.
- W2035226246 cites W2005966299 @default.
- W2035226246 cites W2007606965 @default.
- W2035226246 cites W2028011190 @default.
- W2035226246 cites W2033926103 @default.
- W2035226246 cites W2038941954 @default.
- W2035226246 cites W2040473225 @default.
- W2035226246 cites W2043651274 @default.
- W2035226246 cites W2044132788 @default.
- W2035226246 cites W2044311286 @default.
- W2035226246 cites W2053261180 @default.
- W2035226246 cites W2062477549 @default.
- W2035226246 cites W2074945357 @default.
- W2035226246 cites W2077212878 @default.
- W2035226246 cites W2088982538 @default.
- W2035226246 cites W2093552525 @default.
- W2035226246 cites W2096293129 @default.
- W2035226246 cites W2949698044 @default.
- W2035226246 cites W2950379516 @default.
- W2035226246 cites W2951369717 @default.
- W2035226246 cites W2952265832 @default.
- W2035226246 doi "https://doi.org/10.1039/a804940h" @default.
- W2035226246 hasPublicationYear "1998" @default.
- W2035226246 type Work @default.
- W2035226246 sameAs 2035226246 @default.
- W2035226246 citedByCount "89" @default.
- W2035226246 countsByYear W20352262462012 @default.
- W2035226246 countsByYear W20352262462013 @default.
- W2035226246 countsByYear W20352262462014 @default.
- W2035226246 countsByYear W20352262462015 @default.
- W2035226246 countsByYear W20352262462016 @default.
- W2035226246 countsByYear W20352262462017 @default.
- W2035226246 countsByYear W20352262462018 @default.
- W2035226246 countsByYear W20352262462019 @default.
- W2035226246 countsByYear W20352262462020 @default.
- W2035226246 countsByYear W20352262462021 @default.
- W2035226246 countsByYear W20352262462023 @default.
- W2035226246 crossrefType "journal-article" @default.
- W2035226246 hasAuthorship W2035226246A5002845487 @default.
- W2035226246 hasAuthorship W2035226246A5004486443 @default.
- W2035226246 hasAuthorship W2035226246A5016225060 @default.
- W2035226246 hasAuthorship W2035226246A5019042345 @default.
- W2035226246 hasConcept C106159729 @default.
- W2035226246 hasConcept C111771559 @default.
- W2035226246 hasConcept C142724271 @default.
- W2035226246 hasConcept C155647269 @default.
- W2035226246 hasConcept C162324750 @default.
- W2035226246 hasConcept C178790620 @default.
- W2035226246 hasConcept C185592680 @default.
- W2035226246 hasConcept C201194858 @default.
- W2035226246 hasConcept C204787440 @default.
- W2035226246 hasConcept C2776910235 @default.
- W2035226246 hasConcept C2777000832 @default.
- W2035226246 hasConcept C2780378348 @default.
- W2035226246 hasConcept C34490408 @default.
- W2035226246 hasConcept C71240020 @default.
- W2035226246 hasConcept C71924100 @default.
- W2035226246 hasConcept C7947691 @default.
- W2035226246 hasConceptScore W2035226246C106159729 @default.
- W2035226246 hasConceptScore W2035226246C111771559 @default.
- W2035226246 hasConceptScore W2035226246C142724271 @default.
- W2035226246 hasConceptScore W2035226246C155647269 @default.
- W2035226246 hasConceptScore W2035226246C162324750 @default.
- W2035226246 hasConceptScore W2035226246C178790620 @default.
- W2035226246 hasConceptScore W2035226246C185592680 @default.
- W2035226246 hasConceptScore W2035226246C201194858 @default.
- W2035226246 hasConceptScore W2035226246C204787440 @default.
- W2035226246 hasConceptScore W2035226246C2776910235 @default.
- W2035226246 hasConceptScore W2035226246C2777000832 @default.
- W2035226246 hasConceptScore W2035226246C2780378348 @default.
- W2035226246 hasConceptScore W2035226246C34490408 @default.
- W2035226246 hasConceptScore W2035226246C71240020 @default.
- W2035226246 hasConceptScore W2035226246C71924100 @default.
- W2035226246 hasConceptScore W2035226246C7947691 @default.
- W2035226246 hasIssue "24" @default.
- W2035226246 hasLocation W20352262461 @default.
- W2035226246 hasOpenAccess W2035226246 @default.
- W2035226246 hasPrimaryLocation W20352262461 @default.
- W2035226246 hasRelatedWork W1967369953 @default.
- W2035226246 hasRelatedWork W1984526833 @default.
- W2035226246 hasRelatedWork W2009328128 @default.
- W2035226246 hasRelatedWork W2063125844 @default.
- W2035226246 hasRelatedWork W2081063168 @default.
- W2035226246 hasRelatedWork W2083308364 @default.
- W2035226246 hasRelatedWork W2341011754 @default.