Nucleic acid related compounds. 53. Synthesis and biological evaluation of 2′-deoxy-β-threo-pentofuranosyl nucleosides. "Reversion to starting alcohol" in Barton-type reductions of thionocarbonates

Treatment of selectively 3′,5′-protected β- D -xylofuranosyl nucleosides ( 4 ) with phenyl chlorothionocarbonate and DMAP followed by hydrogenolysis of the resulting (2′-O-phenoxythiocarbonyl) phenyl thionocarbonate esters ( 6 ) with tributylstannane/AIBN, and deprotection, gave 2′-deoxy-β- D -threo...

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Published in:Canadian journal of chemistry 1988-05, Vol.66 (5), p.1258-1262
Main Authors: Robins, Morris J, Madej, Danuta, Hansske, Fritz, Wilson, John S, Gosselin, Gilles, Bergogne, Marie-Christine, Imbach, Jean-Louis, Balzarini, Jan, Clercq, Erik De
Format: Article
Language:English
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Summary:Treatment of selectively 3′,5′-protected β- D -xylofuranosyl nucleosides ( 4 ) with phenyl chlorothionocarbonate and DMAP followed by hydrogenolysis of the resulting (2′-O-phenoxythiocarbonyl) phenyl thionocarbonate esters ( 6 ) with tributylstannane/AIBN, and deprotection, gave 2′-deoxy-β- D -threo-pentofuranosyl nucleosides ( 7 ). Formation of a by-product bis(nucleosid-2′-yl)thionocarbonate dimer ( 8 ) was detected in the uracil nucleoside reaction sequence. Its subsequent reduction provides one explanation for "reversion to starting alcohol" in Barton-type deoxygenation reactions. Only the guanine 2′-deoxynucleoside analogue ( 7 b) had (weak) antiviral activity (against herpes simplex virus type 1).
ISSN:0008-4042
1480-3291
DOI:10.1139/v88-204