Synthesis and crystal structure of 2′,4″ -O-bis(trimethylsilyl)erythromycin a 9-O-(1-isopropoxycyclohexyl) oxime

Jian Hua Liang; Guo Wei Yao

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, Guo Wei Yao^*

^*此作品的通讯作者

化学与化工学院

Beijing Institute of Technology

科研成果: 期刊稿件 › 文章 › 同行评审

2 引用（Scopus）

摘要

The ratio of E/Z of 2′-,4″-O-bis(trimethylsilyl)erythromycin A 9-O-(1-isopropoxycyclohexyl) oxime were much higher prepared in CH ₃CN 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.

源语言	英语
页（从-至）	2527-2534
页数	8
期刊	Heterocycles
卷	60
期	11
DOI	https://doi.org/10.3987/com-03-9864
出版状态	已出版 - 1 11月 2003

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Liang, J. H., & Yao, G. W. (2003). Synthesis and crystal structure of 2′,4″ -O-bis(trimethylsilyl)erythromycin a 9-O-(1-isopropoxycyclohexyl) oxime. Heterocycles, 60(11), 2527-2534. https://doi.org/10.3987/com-03-9864

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abstract = "The ratio of E/Z of 2′-,4″-O-bis(trimethylsilyl)erythromycin A 9-O-(1-isopropoxycyclohexyl) oxime were much higher prepared in CH 3CN 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.",

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N2 - The ratio of E/Z of 2′-,4″-O-bis(trimethylsilyl)erythromycin A 9-O-(1-isopropoxycyclohexyl) oxime were much higher prepared in CH 3CN 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.

AB - The ratio of E/Z of 2′-,4″-O-bis(trimethylsilyl)erythromycin A 9-O-(1-isopropoxycyclohexyl) oxime were much higher prepared in CH 3CN 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.

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Synthesis and crystal structure of 2′,4″ -O-bis(trimethylsilyl)erythromycin a 9-O-(1-isopropoxycyclohexyl) oxime

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