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

Authors

Yousef Ahmadibeni, Columbus State UniversityFollow
Rakesh Tiwari, Chapman UniversityFollow
Gongqin Sun, University of Rhode IslandFollow
Keykavous Parang, Chapman UniversityFollow

Document Type

Article

Publication Date

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.

Comments

This is a pre-copy-editing, author-produced PDF of an article accepted for publication in Organic Letters, volume 11, number 10, 2009 following peer review. The definitive publisher-authenticated version is available online at DOI: 10.1021/ol900320r.

Recommended Citation

Ahmadibeni, Yousef, Rakesh K. Tiwari, Gongqin Sun, and Keykavous Parang. "Synthesis of Nucleoside Mono-, Di-, and Triphosphoramidates from Solid-Phase cyclo Saligenyl Phosphitylating Reagents." Organic letters 11, no. 10 (2009): 2157-2160.
doi: 10.1021/ol900320r

Copyright

American Chemical Society