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Communication | Regular issue | Vol 31, No. 12, 1990, pp.2121-2124
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5616
Chemical Modification of Erythromycins. VIII. A New Effective Route to Clarithromycin (6-O-Methylerythromycin A)

Yoshiaki Watanabe,* Takashi Adachi, Toshifumi Asaka, Masato Kashimura, and Shigeo Morimoto

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

Abstract

Selective O-methylation of the C-6 hydroxyl group of erythromycin A could be satisfactorily achieved by using its 9-oxime derivatives as the starting materials. Thus, 6-O-methylerythromycin A (clarithromycin) was synthesized from 2’-O,3’-N-bis(benzyloxycarbonyl)-N-demethylerythromycin A via its 9-oxime derivative by 6 step.