NDLI: Synthesis of Enantiomerically Pure 1′,2′-cis-dideoxy, -dideoxydidehydro, -ribo and -deoxy Carbocyclic Nucleoside Analogues

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Synthesis of Enantiomerically Pure 1′,2′-cis-dideoxy, -dideoxydidehydro, -ribo and -deoxy Carbocyclic Nucleoside Analogues

Content Provider	Scilit
Author	Meier, Chris Weising, Simon Dekiert, Patrick Schols, Dominique Neyts, Johan
Copyright Year	2018
Description	We describe a short and stereospecific synthesis of different series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues. All-natural nucleobases or their precursors are coupled in a microwave-assisted Mitsunobu-type reaction with enantiomerically pure (1R,2S)-2-(benzyloxymethyl)cyclopent-3-enol. By modifying the cyclopentene scaffold, our synthetic strategy gives access to a series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues of the dideoxy (dd), dideoxydidehydro (d4) or the ribo series. The ribo series is synthesized in a more convenient way compared to a previous route. The deoxy series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues is prepared following an earlier reported approach. This synthesis involves the microwave-assisted coupling of (1R,2S,3S)-3-(benzyloxy)-2-[(benzyloxy)methyl]cyclopentan-1-ol with the appropriate nucleobases.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1609493.pdf
Ending Page	2280
Page Count	15
Starting Page	2266
ISSN	00397881
e-ISSN	1437210X
DOI	10.1055/s-0037-1609493
Journal	Synthesis
Issue Number	11
Volume Number	50
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2018-04-12
Access Restriction	Open
Subject Keyword	Journal: Synthesis Organic Chemistry Mitsunobu Coupling 2′-cis-substitution Microwave Reaction
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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