Вид документа : Статья из журнала Шифр издания : 54/S 98 Автор(ы) : Khalymbadzha I. A., Shestakova T.S., Subbotina J.O., Eltsov O. S., Musikhina A. A, Rusinov V. L., Chupakhin O. N., Karpenko I. L., Jasko M. V., Kukhanova M. K., Deev S. L. Заглавие : Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidin-7-ones by one-step Vorbrüggen glycosylation [Электронный ресурс] Место публикации : Tetrahedron. - 2014. - Vol.70, №6. - С. 1298-1305 Систем. требования: http://ac.els-cdn.com/S0040402013019194/1-s2.0-S0040402013019194-main.pdf?_tid=eef77b26-b32a-11e3-ba34-00000aacb35e&acdnat=1395648453_99f8c77e049775184b5db6b93d0988c2 Примечания : Bibliogr. : p. 1304-1305 (29 ref.). - 24.03.2014 ББК : 54 Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ Ключевые слова (''Своб.индексиров.''): acyclovir analogues--1,2,4-triazolo[1,5-a]pyrimidines--tmsotf Аннотация: 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 (Vorbrüggen 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 ZnCl2 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 Vorbrüggen proced Доп.точки доступа: Khalymbadzha, I. A.; Shestakova, T.S.; Subbotina, J.O.; Eltsov, O. S.; Musikhina, A. A; Rusinov, V. L.; Chupakhin, O. N.; Karpenko, I. L.; Jasko, M. V.; Kukhanova, M. K.; Deev , S. L.