Assessment of 4-Nitrogenated Benzyloxymethyl Groups for 2'-Hydroxyl Protection in Solid-Phase RNA Synthesis

J Cieslak, JS Kauffman, MJ Kolodziejski, JR Lloyd…

Index: Cieslak, Jacek; Kauffman, Jon S.; Kolodziejski, Michelle J.; Lloyd, John R.; Beaucage, Serge L. Organic Letters, 2007 , vol. 9, # 4 p. 671 - 674

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Citation Number: 23

Abstract

The search for a 2'-OH protecting group that would impart ribonucleoside phosphoramidites with coupling kinetics and coupling efficiencies comparable to those of deoxyribonucleoside phosphoramidites led to an assessment of 2'-O-(4-nitrogenated benzyloxy) methyl groups through solid-phase RNA synthesis using phosphoramidites 2a-d, 12a, and 14a. These phosphoramidites exhibited rapid and efficient coupling properties. Particularly ...