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• W2912790821 abstract "Two approaches for C4 modifications of silyl-protected thymidine, 2'-deoxyuridine, and 3'-azido-2',3'-dideoxythymidine (AZT) are described. In both, nucleoside amide activation with 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and DBU yields O4 -(benzotriazol-1-yl) derivatives. These in situ-formed intermediates are reacted with various nucleophiles, resulting in C4 modifications. In the two-step, one-pot approach, the O4 -(benzotriazol-1-yl) nucleoside intermediates are initially produced by reactions of the nucleosides with BOP and DBU in THF. This step is fast and typically complete within 30 min. Subsequently, the O4 -(benzotriazol-1-yl) derivatives are reacted with nucleophiles, such as aliphatic and aromatic amines, thiols, and alcohols, under appropriate conditions. Workup, isolation, and purification lead to the desired C4-modified pyrimidine nucleosides in good to excellent yields. In the one-step approach, the nucleosides are reacted with BOP and DBU, in the presence of the nucleophile (only aliphatic and aromatic amines, and thiols have been tested). Where comparisons are possible, the one-step approach is generally superior. © 2019 by John Wiley & Sons, Inc." @default.
• W2912790821 created "2019-02-21" @default.
• W2912790821 creator A5010134206 @default.
• W2912790821 creator A5087369114 @default.
• W2912790821 date "2019-01-28" @default.
• W2912790821 modified "2023-09-25" @default.
• W2912790821 title "Facile Modifications at the C4 Position of Pyrimidine Nucleosides via In Situ Amide Activation with 1 H ‐Benzotriazol‐1‐yloxy‐tris(dimethyl‐amino)phosphonium Hexafluorophosphate" @default.
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• W2912790821 doi "https://doi.org/10.1002/cpnc.73" @default.
• W2912790821 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6834435" @default.
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