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- W2015331168 abstract "Abstract New acyclovir analogues were obtained by reaction of 1,2,4-triazolo[1,5- a ]pyrimidin-7-ones 4a – i with (2-acetoxyethoxy)methyl acetate 5 in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as catalyst (Vorbruggen procedure). Coupling between compounds 4a – f and 5 led to a mixture of N3- and N4-isomers 6 and 7 , respectively. On the contrary, the reaction of compounds 4g – i with 5 proceeded selectively with formation of N3-isomers only. It was found that the ratio of 6a – f and 7a – f depends on the presence or the absence of N , O -bis(trimethylsilyl)acetamide (BSA). Glycosylated products 6a – f and 7a – f underwent reversible isomerization under TMSOTf treatment. The ratio of glycosylated products of the coupling reaction between 4 and 5 was thermodynamically controlled. A similar reaction occurred if ZnCl 2 was chosen as a catalyst, although lower yields of the acyclic analogues of nucleosides were observed. The glycosylation of other purines (adenine and guanine) can be achieved via the non-BSA modification of the Vorbruggen procedure." @default.
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- W2015331168 date "2014-02-01" @default.
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- W2015331168 title "Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidin-7-ones by one-step Vorbrüggen glycosylation" @default.
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- W2015331168 doi "https://doi.org/10.1016/j.tet.2013.12.051" @default.
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