Tetrahedron

Convenient synthesis of N 2-isobutyryl-2′-O-methyl guanosine by efficient alkylation of O 6-trimethylsilylethyl-3′, 5′-di-tert-butylsilanediyl guanosine

I Zlatev, JJ Vasseur, F Morvan

Index: Zlatev, Ivan; Vasseur, Jean-Jacques; Morvan, Francois Tetrahedron, 2007 ,  vol. 63,  # 45  p. 11174 - 11178

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Citation Number: 7

Abstract

We present a novel route for the synthesis of N2-isobutyryl-2′-O-methyl guanosine, introducing 3′, 5′-di-tert-butylsilyl and O6-trimethylsilylethyl groups as efficient protections during the 2′-O-methylation step with NaH/CH3I. These protections were then removed simultaneously in a single step with TBAF. The eight-step synthesis is easy to perform, employing convenient commercially available reagents; crude mixtures are of satisfying ...