A facile synthesis of 9-(1,3-dihydroxy-2-propoxymethyl)guanine (ganciclovir) from guanosine
The potent and selective antiviral drug ganciclovir (6) has been synthesized in two steps via transpurination of fully acetylated guanosine (1) in the presence of 1,3-diacetoxy-2-(acetoxymethoxy)propane (2), followed by deacetylation in aqueous ammonia. The transpurination reaction also provides valuable side products, tetra-O-acetyl-β-D-ribofuranose (5) and the 7-regioisomer of triacetylganciclovir (4); the latter product can be converted to the desired 9-isomer in a thermal 7 ? 9 isomerization.
Boryski, Jerzy,Golankiewicz, Bozenna
p. 625 - 628
(2007/10/03)
Biologically active acyclonucleoside analogues. II. The synthesis of 9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]guanine (BIOLF-62)
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Ogilvie,Cheriyan,Radatus
p. 3005 - 3010
(2007/10/02)
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