Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a] pyrimidin-7-ones by one-step Vorbrüggen glycosylation / 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. // Tetrahedron. - 2014. - V. 70, l. 6. - P. 1298-1305.

ISSN:
00404020
Type:
Article
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 (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 procedure. © 2014 Elsevier Ltd. All rights reserved.
Author keywords:
1,2,4-Triazolo[1,5-a]pyrimidine-7-one; Acyclovir analogues; Herpes simplex virus; Regioselectivity; TMSOTf; Transglycosylation; Vorbrüggen glycosylation
Index keywords:
(2 acetoxyethoxy)methyl acetate; 1,2,4 triazolo [1,5 alpha]pyrimidin 7 one; 3 [(2 acetoxyethoxy)methyl] 5 methyl 1,2,4 triazolo[1,5alpha]pyrimidin 7 one; 3 [(2 acetoxyethoxy)methyl] 5 phenyl 1,2,4 tri
DOI:
10.1016/j.tet.2013.12.051
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Affiliations Ural Federal University, 19 Mira Street, Ekaterinburg 620002, Russian Federation; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoy Street, Ekaterinburg 620219, Russian Federation; Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilov Street, Moscow 119991, Russian Federation
Author Keywords 1,2,4-Triazolo[1,5-a]pyrimidine-7-one; Acyclovir analogues; Herpes simplex virus; Regioselectivity; TMSOTf; Transglycosylation; Vorbrüggen glycosylation
Chemicals/CAS trifluoromethanesulfonic acid, 1493-13-6; zinc chloride, 7646-85-7
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Correspondence Address Deev, S.L.; Ural Federal University, 19 Mira Street, Ekaterinburg 620002, Russian Federation; email: deevsl@yandex.ru
CODEN TETRA
Language of Original Document English
Abbreviated Source Title Tetrahedron
Source Scopus