Synthesis of Nucleoside Mono-, Di-, and Triphosphoramidates from Solid-Phase cycloSaligenyl Phosphitylating Reagents
Date of Original Version
Chloromethyl polystyrene resin was reacted with 5-hydroxysalicylaldehyde in the presence of potassium carbonate to afford polymer-bound 2-hydroxybenzaldehyde. Subsequent reduction with borane solution produced polymer-bound 2-hydroxybenzyl alcohol. The reaction of immobilized 2-hydroxybenzyl alcohol with appropriate phosphitylating reagents yielded solid-phase cycloSaligenyl mono-, di-, and triphosphitylating reagents, which were reacted with unprotected nucleosides, followed by iodine oxidation, deprotection of cyanoethoxy groups, and the basic cleavage, respectively, to afford 5′-O-nucleoside mono-, di-, and triphosphoramidates in 52−73% overall yield.
Ahmadibeni, Y., Tiwari, R. K., Sun, G., & Parang, K. (2009). Synthesis of Nucleoside Mono-, Di-, and Triphosphoramidates from Solid-Phase cycloSaligenyl Phosphitylating Reagents. Org. Lett. 11(10), 2157-2160. doi: 10.1021/ol900320r
Available at: https://doi.org/10.1021/ol900320r
Yousef Ahmadibeni, Rakesh K. Tiwari and Keykavous Parang are from the Department of Biomedical and Pharmaceutical Sciences.
Gongqin Sun is from the Department of Cell and Molecular Biology.
This is a pre-publication author manuscript of the final, published article.
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