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Approach to Artificial Nucleosides from Glycoside Isothiocyanates: Synthesis of Original N‐Glycosylated Heterostructures by Cyclocondensation Reactions
Author(s) -
Grosjean Sylvain,
Julienne Karine,
Gouin Sébastien G.,
Deniaud David
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903391
Subject(s) - pyrimidine , isothiocyanate , nucleoside , purine , chemistry , glycoside , stereochemistry , bicyclic molecule , yield (engineering) , combinatorial chemistry , organic chemistry , materials science , metallurgy , enzyme
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 13 a‐m were synthesized with a 30% yield on average, over 8 or 9 steps from one of the isothiocyanates 4 a‐c . These elaborated targets were fully characterized.