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Note | Regular issue | Vol 60, No. 11, 2003, pp.2527-2534
Published online, 5th September, 2003
DOI: 10.3987/COM-03-9864
Synthesis and Crystal Structure of 2’,4”-O-Bis(trimethylsilyl)erythromycin A 9-O-(1-Isopropoxycyclohexyl) Oxime

Jian-Hua Liang and Guo-Wei Yao*

*School of Life Science and Technology, Beijing Institute of Technology, Beijing 100081, China

Abstract

The ratio of E/Z of 2’-,4”-O-bis(trimethylsilyl)erythromycin A 9-O-(1-isopropoxycyclohexyl) oxime were much higher prepared in CH3CN than those in CH2Cl2. And the ratio would increase with elevation of temperature. Compared with 2’-OH, 4”-OH was liable to be silylated in the presence of 1,1,1,3,3,3-hexamethyldisilizane and an NH4+. The crystal structure of E-title compound was determined by single-crystal X-Ray structure analysis to elucidate the origin of regioselectivity occurring at 6-hydroxyl group in the O-methylation of erythromycin A.