The water-soluble alkylating agent: 1-oxido-pyridin-2-yldiazomethane (I) introduces the 1-oxido-pyridin-2-ylmethyl protecting group into acidic substances (pKa < 9·8) including nucleotides; it can be removed by treatment with acetic anhydride followed by methanolic ammonia.
T. Endo, K. Ikeda, Y. Kawamura and Y. Mizuno, J. Chem. Soc., Chem. Commun., 1973, 673 DOI: 10.1039/C39730000673
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