Synthesis of Nucleoside Mono-, Di-, and Triphosphoramidates from Solid-Phase cycloSaligenyl Phosphitylating Reagents

Authors

Yousef Ahmadibeni, University of Rhode Island
Rakesh K. Tiwari, University of Rhode Island
Gongqin Sun, University of Rhode IslandFollow
Keykavous Parang, University of Rhode IslandFollow

Document Type

Article

Date of Original Version

2009

Abstract

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.

Citation/Publisher Attribution

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

Comment

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.