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

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 synthesi...

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Bibliographic Details
Published in:	Organic letters Vol. 9; no. 4; pp. 671 - 674
Main Authors:	Cieślak, Jacek, Kauffman, Jon S, Kolodziejski, Michelle J, Lloyd, John R, Beaucage, Serge L
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 15-02-2007
Subjects:	Benzyl Compounds - chemistry Chromatography, High Pressure Liquid Indicators and Reagents Kinetics Methylation Nitro Compounds - chemistry RNA - chemical synthesis Thymidine - chemistry Uridine - chemistry
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Summary:	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 noteworthy is the cleavage of the 2‘-O-[4-(N-methylamino)benzyloxy]methyl groups in 0.1 M AcOH, which led to U19dT within 15 min at 90 °C.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol0629824