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Paper | Regular issue | Vol 31, No. 2, 1990, pp.305-319
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5236
Chemical Modification of Erythromycins VII. Molecular Rearrangement Observed during Chemical Modification Study of the Desosamine Unit of Erythromycins

Shigeo Morimoto, Takashi Adachi, Yoshiaki Watanaba,* and Sadafumi Omura

*Research Center, Taisho Pharmaceutical Co., Ltd., 1-403 Yoshino-Cho, Ohmiya, Saitama 330-8530, Japan

Abstract

The reaction of 2’-O-methanesulfonylerythromycin A derivatives (2) with a variety of nucleophilic reagents gave 2’-dimethylamino-3’-substituted derivatives (3). The reaction took place with neighboring group-participated nucleophilic substitution involoving migration of participating 3’-dimethylamino group. This migration was also observed in the case of N-oxide of the dimethylamino group.