TY - JOUR
T1 - Innovative Strategies for the Construction of Diverse 1′-Modified C-Nucleoside Derivatives
AU - Panda, Subhankar
AU - Poudel, Tej Narayan
AU - Hegde, Pooja
AU - Aldrich, Courtney C.
N1 - Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/12/3
Y1 - 2021/12/3
N2 - Modified C-nucleosides have proven to be enormously successful as chemical probes to understand fundamental biological processes and as small-molecule drugs for cancer and infectious diseases. Historically, the modification of the glycosyl unit has focused on the 2′-, 3′-, and 4′-positions as well as the ribofuranosyl ring oxygen. By contrast, the 1′-position has rarely been studied due to the labile nature of the anomeric position. However, the improved chemical stability of C-nucleosides allows the modification of the 1′-position with substituents not found in conventional N-nucleosides. Herein, we disclose new chemistry for the installation of diverse substituents at the 1′-position of C-nucleosides, including alkyl, alkenyl, difluoromethyl, and fluoromethyl substituents, using the 4-amino-7-(1′-hydroxy-d-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine scaffold as a representative purine nucleoside mimetic.
AB - Modified C-nucleosides have proven to be enormously successful as chemical probes to understand fundamental biological processes and as small-molecule drugs for cancer and infectious diseases. Historically, the modification of the glycosyl unit has focused on the 2′-, 3′-, and 4′-positions as well as the ribofuranosyl ring oxygen. By contrast, the 1′-position has rarely been studied due to the labile nature of the anomeric position. However, the improved chemical stability of C-nucleosides allows the modification of the 1′-position with substituents not found in conventional N-nucleosides. Herein, we disclose new chemistry for the installation of diverse substituents at the 1′-position of C-nucleosides, including alkyl, alkenyl, difluoromethyl, and fluoromethyl substituents, using the 4-amino-7-(1′-hydroxy-d-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine scaffold as a representative purine nucleoside mimetic.
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U2 - 10.1021/acs.joc.1c01920
DO - 10.1021/acs.joc.1c01920
M3 - Article
C2 - 34756029
AN - SCOPUS:85119436232
SN - 0022-3263
VL - 86
SP - 16625
EP - 16640
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -