A New Method for Removal of Modified Trityl and Pixyl Groups by Use of an Acid Species Generated by Reaction of Diethyl Oxomalonate with Methanol

Abstract

Diethyl oxomalonate (DEOM) was found to exhibit unique properties as a new type of detritylating reagent in the presence of methanol. A variety of deoxyribonucleoside derivatives protected with modified trityl groups were allowed to react with DEOM. The ease of detritylation highly depended on the basicity of protected bases of adenine, guanine and cytosine. Inhibitory effects of various amines possessing the pKa values between 0.79–10.87 on the present detritylation were studied. Several mechanistic considerations were also discussed on the basis of ¹H and ¹³C NMR studies of the DEOM-Methanol adduct.