Matches in SemOpenAlex for { <https://semopenalex.org/work/W2015352441> ?p ?o ?g. }
- W2015352441 endingPage "4648" @default.
- W2015352441 startingPage "4640" @default.
- W2015352441 abstract "Abstract Efficient methodologies based on consecutive radical reactions for the preparation of cyclonucleosides 5 and 13 are reported. The reactions were performed on modified thymidine and 2′‐deoxyadenosine substrates using (TMS) 3 SiH as the reducing agent. The protected 5′‐carbaldehyde 3 afforded the cyclonucleoside 4 in 85 % yield and in a diastereoisomeric ratio 4a / 4b = 3:7. The mono‐desilylation at the 5′‐ O position of these cyclonucleosides has been successfully achieved by UV irradiation affording quantitatively derivatives 5a and 5b . The protected 5′‐carbaldehyde 10 afforded the cyclonucleoside 12 in 70–75 % yield as a single diastereoisomer (5′ R ) either in deoxygenated solution, followed by in situ oxidation of the reaction mixture by chloranil, or in aerobic conditions. The photochemical 5′‐ O ‐desilylation of 12 has been obtained in 56 % yield affording the cyclopurine 13 . The reaction mechanisms have been studied in some detail using a variant of the radical clock methodology. The C5′ radical 6 or 15 , generated by addition of the (TMS) 3 Si · radical to the corresponding aldehyde, undergoes a 6‐ exo‐trig cyclization on the base moiety prior to termination. The rate constants for both 6‐ exo‐trig radical cyclizations have been estimated to be close to 10 5 s –1 at 86 °C, the cyclization on the purine moiety being 4–5 times faster than that on the pyrimidine group. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)" @default.
- W2015352441 created "2016-06-24" @default.
- W2015352441 creator A5035024636 @default.
- W2015352441 creator A5050716707 @default.
- W2015352441 creator A5067024672 @default.
- W2015352441 creator A5071083060 @default.
- W2015352441 date "2005-10-17" @default.
- W2015352441 modified "2023-10-05" @default.
- W2015352441 title "Radical Cyclization Approach to Cyclonucleosides" @default.
- W2015352441 cites W1482793314 @default.
- W2015352441 cites W1489408430 @default.
- W2015352441 cites W1971434477 @default.
- W2015352441 cites W1981120794 @default.
- W2015352441 cites W1985964767 @default.
- W2015352441 cites W1987952194 @default.
- W2015352441 cites W1991202602 @default.
- W2015352441 cites W1999504969 @default.
- W2015352441 cites W2001431653 @default.
- W2015352441 cites W2012298510 @default.
- W2015352441 cites W2013615285 @default.
- W2015352441 cites W2019295542 @default.
- W2015352441 cites W2024714314 @default.
- W2015352441 cites W2025599592 @default.
- W2015352441 cites W2027604638 @default.
- W2015352441 cites W2030666445 @default.
- W2015352441 cites W2038389845 @default.
- W2015352441 cites W2044409196 @default.
- W2015352441 cites W2049392271 @default.
- W2015352441 cites W2050844955 @default.
- W2015352441 cites W2057945382 @default.
- W2015352441 cites W2059155645 @default.
- W2015352441 cites W2061081886 @default.
- W2015352441 cites W2067987221 @default.
- W2015352441 cites W2069626502 @default.
- W2015352441 cites W2071982166 @default.
- W2015352441 cites W2072490638 @default.
- W2015352441 cites W2074552403 @default.
- W2015352441 cites W2082338217 @default.
- W2015352441 cites W2103253047 @default.
- W2015352441 cites W2113912029 @default.
- W2015352441 cites W2158442028 @default.
- W2015352441 cites W2332378261 @default.
- W2015352441 cites W2475884896 @default.
- W2015352441 cites W2494519367 @default.
- W2015352441 cites W2951284448 @default.
- W2015352441 cites W612383473 @default.
- W2015352441 doi "https://doi.org/10.1002/ejoc.200500398" @default.
- W2015352441 hasPublicationYear "2005" @default.
- W2015352441 type Work @default.
- W2015352441 sameAs 2015352441 @default.
- W2015352441 citedByCount "24" @default.
- W2015352441 countsByYear W20153524412012 @default.
- W2015352441 countsByYear W20153524412013 @default.
- W2015352441 countsByYear W20153524412014 @default.
- W2015352441 countsByYear W20153524412017 @default.
- W2015352441 countsByYear W20153524412018 @default.
- W2015352441 countsByYear W20153524412022 @default.
- W2015352441 crossrefType "journal-article" @default.
- W2015352441 hasAuthorship W2015352441A5035024636 @default.
- W2015352441 hasAuthorship W2015352441A5050716707 @default.
- W2015352441 hasAuthorship W2015352441A5067024672 @default.
- W2015352441 hasAuthorship W2015352441A5071083060 @default.
- W2015352441 hasConcept C134121241 @default.
- W2015352441 hasConcept C138716334 @default.
- W2015352441 hasConcept C139066938 @default.
- W2015352441 hasConcept C155647269 @default.
- W2015352441 hasConcept C161790260 @default.
- W2015352441 hasConcept C178790620 @default.
- W2015352441 hasConcept C185592680 @default.
- W2015352441 hasConcept C191897082 @default.
- W2015352441 hasConcept C192562407 @default.
- W2015352441 hasConcept C20327893 @default.
- W2015352441 hasConcept C2776568683 @default.
- W2015352441 hasConcept C2779321679 @default.
- W2015352441 hasConcept C2779825165 @default.
- W2015352441 hasConcept C2780995637 @default.
- W2015352441 hasConcept C44228677 @default.
- W2015352441 hasConcept C521977710 @default.
- W2015352441 hasConcept C71240020 @default.
- W2015352441 hasConceptScore W2015352441C134121241 @default.
- W2015352441 hasConceptScore W2015352441C138716334 @default.
- W2015352441 hasConceptScore W2015352441C139066938 @default.
- W2015352441 hasConceptScore W2015352441C155647269 @default.
- W2015352441 hasConceptScore W2015352441C161790260 @default.
- W2015352441 hasConceptScore W2015352441C178790620 @default.
- W2015352441 hasConceptScore W2015352441C185592680 @default.
- W2015352441 hasConceptScore W2015352441C191897082 @default.
- W2015352441 hasConceptScore W2015352441C192562407 @default.
- W2015352441 hasConceptScore W2015352441C20327893 @default.
- W2015352441 hasConceptScore W2015352441C2776568683 @default.
- W2015352441 hasConceptScore W2015352441C2779321679 @default.
- W2015352441 hasConceptScore W2015352441C2779825165 @default.
- W2015352441 hasConceptScore W2015352441C2780995637 @default.
- W2015352441 hasConceptScore W2015352441C44228677 @default.
- W2015352441 hasConceptScore W2015352441C521977710 @default.
- W2015352441 hasConceptScore W2015352441C71240020 @default.
- W2015352441 hasIssue "21" @default.
- W2015352441 hasLocation W20153524411 @default.