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Synthesis of (+/-)-2',3'-Didehydro-2',3'-dideoxy Nucleosides via a Modified Prins Reaction and Palladium(0) Catalysed Coupling

DOI: 10.1039/P19910002603

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2603 - 2604 (1991)

Update date:2022-08-25

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Authors:

Saville-Stones, Elizabeth A.Saville-Stones, Elizabeth A.

Lindell, Stephen D.Lindell, Stephen D.

Jennings, Neil S.Jennings, Neil S.

Head, John C.Head, John C.

Ford, Mark J.Ford, Mark J.

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Article abstract of DOI:10.1039/P19910002603

Cyclopentenyl allylic acetates have been prepared in diastereoisomerically enriched form by modification of the Prins reaction.Palladium(0) catalysed coupling between these allylic acetates and a heteroaromatic base provides a highly convergent and direct route for synthesising carbocyclic 2',3'-didehydro-2',3'-dideoxy nucleosides.The method is exemplified by the coupling reaction with adenine which yields (+/-)-2',3'-didehydro-2',3'-dideoxyaristeromycin 5'-O-acetate 22 in 50percent yield.This has been converted in two steps into (+/-)-aristeromycin triacetate 5.

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Product name:[(1S,4R)-4-(6-amino-9H-purin-9-yl)cyclopent-2-en-1-yl]methanol

Cas No:118237-82-4

118237-82-4

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