Unit

UNIT 1.26 Two-Step, One-Pot Synthesis of Inosine, Guanosine, and 2′-Deoxyguanosine O6-Ethers via Intermediate O6-(Benzotriazol-1-yl) Derivatives

  1. Hari Prasad Kokatla,
  2. Mahesh K. Lakshman

Published Online: 1 JUN 2012

DOI: 10.1002/0471142700.nc0126s49

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Kokatla, H. P. and Lakshman, M. K. 2012. Two-Step, One-Pot Synthesis of Inosine, Guanosine, and 2′-Deoxyguanosine O6-Ethers via Intermediate O6-(Benzotriazol-1-yl) Derivatives. Current Protocols in Nucleic Acid Chemistry. 49:1.26:1.26.1–1.26.16.

Author Information

  1. The City College and The City University of New York, New York City, New York

Publication History

  1. Published Online: 1 JUN 2012

Abstract

A simple method for the etherification at the O6-position of silyl-protected inosine, guanosine, and 2′-deoxyguanosine is described. Typically, a THF solution of the silylated nucleoside is treated with 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and Cs2CO3 under a nitrogen atmosphere. Conversion to the O6-(benzotriazol-1-yl) ethers occurs within about 10 min for inosine, and within about 60 min for guanosine and 2′-deoxyguanosine. Then, for reaction with alcohols, the reaction mixture is evaporated and the O6-(benzotriazol-1-yl) ether is treated with Cs2CO3 and an appropriate alcohol, at room temperature. On the other hand, for reaction with phenols, Cs2CO3 and the appropriate phenol are added to the reaction mixture without evaporation, and the reaction is carried out at 70°C. Subsequently, workup, isolation, and purification lead to the requisite O6-alkyl or O6-aryl ethers in good to excellent yields. Curr. Protoc. Nucleic Acid Chem. 49:1.26.1-1.26.16. © 2012 by John Wiley & Sons, Inc.

Keywords:

  • inosine;
  • guanosine;
  • 2′-deoxyguanosine;
  • BOP;
  • reactive nucleosides;
  • ethers;
  • benzotriazolyl