Article Dans Une Revue ChemistrySelect Année : 2019

Approach to Artificial Nucleosides from Glycoside Isothiocyanates: Synthesis of Original N‐Glycosylated Heterostructures by Cyclocondensation Reactions

Résumé

Unusual purine nucleoside analogues were synthesized, using the well-tried methodology in heterocyclic chemistry. This result expands the scope of accessible N-glycosylated heterocyclic structures. Pyrimidine, and bicyclic pyrimido[1,2-a]pyrimidine nucleoside analogues were prepared from common glycoside isothiocyanate precursors. Key cyclization steps were all based on a cyclocondensation reaction involving an activated heterodienic chain. Finally, thirteen pyrimido[1.2-a]pyrimidine nucleoside analogues 13a-m were synthesized with a 30% yield on average, over 8 or 9 steps from one of the isothiocyanates 4a-c. These elaborated targets were fully characterized.

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hal-03003107 , version 1 (16-11-2020)

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Sylvain Grosjean, Karine Julienne, Sébastien Gouin, David Deniaud. Approach to Artificial Nucleosides from Glycoside Isothiocyanates: Synthesis of Original N‐Glycosylated Heterostructures by Cyclocondensation Reactions. ChemistrySelect, 2019, 4 (42), pp.12232-12235. ⟨10.1002/slct.201903391⟩. ⟨hal-03003107⟩
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