7602-01-9Relevant articles and documents
Synthesis of potentially prebiotic RNA precursors: Cytosine and guanine derivatives
Sutherland, John D.,Whitfield, J. Nicole
, p. 1451 - 1454 (1997)
The chemical synthesis of two potentially prebiotic monomers of RNA containing cytosine and guanine is reported.
Synthesis of the hepatitis B nucleoside analogue lagociclovir valactate
Brodszki, Martin,Baeckstroem, Birthe,Malmgren, Hakan,Wennerberg, Johan,Larsson, Torbjoern,Pelcman, Mikael,Waehling, Horst,Wallberg, Hans,Horvath, Karol
experimental part, p. 1027 - 1032 (2012/01/04)
2′,3′-Dideoxy-3′-fluoro-5-O-[(S)-(+)-2-(l-valyloxy) -propionyl guanosine (lagociclovir valactate) is a prodrug of 3′-fluoro-2′,3′-dideoxyguanosine with high oral bioavailability in humans and potent activity against hepatitis B virus (HBV). A five-step synthesis of lagocyclovir valactate starting from 2-amino-6-chloropurine is described. The synthesis was performed at kilogram scale, and the target nucleoside prodrug was isolated as the hemisulphate salt with an overall yield of 23%. The major challenges were N-glycosylation of a 2-deoxyfluorosugar, which required separation of α- and β-anomers, and deprotection of the penultimate intermediate by hydrogenation.
Process for preparing 2-acetylamino-6-chloropurine
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, (2008/06/13)
[OBJECT] To provide an intended product of high quality at low production costs in a yield higher than in ordinary processes by using an inexpensive catalyst or a catalyst which can be readily recovered. [ARRANGEMENT] A process for preparing 2-acetylamino-6-chloropurine comprises suspending 2,9-diacetylguanine or 2-acetylguanine in a polar inert solvent, reacting with phosphorus oxychloride in the presence of a water-insoluble tertiary amine and either ammonium chloride or a hydrochloride of the tertiary amine, and hydrolyzing the resultant reaction product to obtain 2-acetylamino-6-chloropurine.