Author: Qi Liu; Amita Gupta; Ayse Okesli-Armlovich; Wenjie Qiao; Curt R. Fischer; Mark Smith; Jan E. Carette; Michael C. Bassik; Chaitan Khosla
Title: Enhancing the Antiviral Efficacy of RNA-Dependent RNA Polymerase Inhibition by Combination with Modulators of Pyrimidine Metabolism Document date: 2020_3_25
ID: 1zk64gsg_10
Snippet: Next, we turned to synthesis of CPU analogs modified at the C5' position of the cyclopentenyl moiety ( Figure 2B ). Selective deprotection of TBDPS with TBAF revealed the primary hydroxyl group (Song et al., 2001) , which was then methylated in the presence of Ag2O (Cosme G. Francisco et al., 2001) to afford the protected 5'-methoxy-CPU. Alternatively, the alcohol could be converted to a terminal fluoride with diethylamino sulfurotrifluoride (DAS.....
Document: Next, we turned to synthesis of CPU analogs modified at the C5' position of the cyclopentenyl moiety ( Figure 2B ). Selective deprotection of TBDPS with TBAF revealed the primary hydroxyl group (Song et al., 2001) , which was then methylated in the presence of Ag2O (Cosme G. Francisco et al., 2001) to afford the protected 5'-methoxy-CPU. Alternatively, the alcohol could be converted to a terminal fluoride with diethylamino sulfurotrifluoride (DAST) , resulting in protected 5'-fluoro CPU. Mesylation or acetylation of 5, followed by NaN3 substitution (Schaudt and Blechert, 2003) or Pd(OH)2/C catalyzed hydrogenation (Bianco et al., 1989) afforded the protected 5'-azido-and 5'deoxy-CPU, respectively. The resulting protected intermediates were treated with methanolic ammonia and/or HCl to provide analogs 6,7, 9 and 11. MeI, acetone; f) DAST, CH2Cl2; g) MsCl, Et3N, CH2Cl2; h) NaN3, DMF; i) AcCl, CH2Cl2; j) Pd(OH)2, cyclohexene, ethanol. TBDPS=tert-Butyldiphenyl silyl; Bz=Benzoyl; TBAF=Tetra-n-butylammonium fluoride, DAST=Diethylaminosulfur trifluoride, Ms= Methanesulfonyl, Ac=acetyl.
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