Copper(II)nitrate catalyzed regioselective protection of primary alcohols with 4,4′-dimethoxytrityl and 2,7-dimethyl-9-phenyl xanthen-9-yl groups in nucleosides and carbohydrates

ABSTRACT

Regioselective protection of primary hydroxyl group in nucleoside and carbohydrate analogs was accomplished using dimethoxytrityl alcohol (DMTr-OH) or dimethylpixyl alcohol (DMPx-OH) in presence of copper(II)nitrate as a Lewis acid catalyst. Excellent selectivity was observed for the protection of primary hydroxyl group over secondary while glycosidic bond remain unaffected. Utility of this methodology was further exemplified via DMTr- and DMPx-protection of alipahtic acyclic and cyclic diols.

KEYWORDS:

• nucleosides
• protecting groups
• regioselectivity
• lewis acid catalysis
• DMTr-group and DMPx-group

Acknowledgments

The authors are thankful to Dr. P.Y. Reddy for his encouragement and valuable suggestions. S.P. thanks the Director National Institute of Technology, Raipur.