Synthesis and separation of the clarithromycin A(E)-9-O-methyl oxime

Yi Jiao Nie; Ling Li Li; Cong Liu; Rong Ji Dai; Li Quan Sun; Guo Wei Yao

Synthesis and separation of the clarithromycin A(E)-9-O-methyl oxime

Yi Jiao Nie, Ling Li Li, Cong Liu, Rong Ji Dai, Li Quan Sun, Guo Wei Yao^*

^*此作品的通讯作者

生命学院

Beijing Institute of Technology

科研成果: 期刊稿件 › 文章 › 同行评审

1 引用（Scopus）

摘要

To control the commercial production of clarithromycin, clarithromycin A(E)9-O-methyl oxime was synthesized using clarithromycin A oxime as the raw material by three steps: protection of 2'-OH and 4″-OH with TMS, methylation and de-protection of TMS. The structure was identified by ¹H NMR, ¹³C NMR and HPLC analysis was conducted. Experimental results show that the reactions are greatly affected by catalyst, solvent and pH value. The parameters of HPLC are as follows. The mobile phase is ACN/KH ₂PO ₄ aqueous solution (V/V=45/55), wavelength is 210 nm, temperature is 30°C and the velocity of flow is 1.0 mL/min. This synthesized compound is of benefit to control the commercial production of clarithromycin.

源语言	英语
页（从-至）	102-105
页数	4
期刊	Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology
卷	32
期	1
出版状态	已出版 - 1月 2012

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title = "Synthesis and separation of the clarithromycin A(E)-9-O-methyl oxime",

abstract = "To control the commercial production of clarithromycin, clarithromycin A(E)9-O-methyl oxime was synthesized using clarithromycin A oxime as the raw material by three steps: protection of 2'-OH and 4″-OH with TMS, methylation and de-protection of TMS. The structure was identified by 1H NMR, 13C NMR and HPLC analysis was conducted. Experimental results show that the reactions are greatly affected by catalyst, solvent and pH value. The parameters of HPLC are as follows. The mobile phase is ACN/KH 2PO 4 aqueous solution (V/V=45/55), wavelength is 210 nm, temperature is 30°C and the velocity of flow is 1.0 mL/min. This synthesized compound is of benefit to control the commercial production of clarithromycin.",

keywords = "Clarithromycin A, Clarithromycin A 9 oxime, Clarithromycin A(E)-9-O-methyl oxime",

author = "Nie, {Yi Jiao} and Li, {Ling Li} and Cong Liu and Dai, {Rong Ji} and Sun, {Li Quan} and Yao, {Guo Wei}",

year = "2012",

month = jan,

language = "English",

volume = "32",

pages = "102--105",

journal = "Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology",

issn = "1001-0645",

publisher = "Beijing Institute of Technology",

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TY - JOUR

T1 - Synthesis and separation of the clarithromycin A(E)-9-O-methyl oxime

AU - Nie, Yi Jiao

AU - Li, Ling Li

AU - Liu, Cong

AU - Dai, Rong Ji

AU - Sun, Li Quan

AU - Yao, Guo Wei

PY - 2012/1

Y1 - 2012/1

N2 - To control the commercial production of clarithromycin, clarithromycin A(E)9-O-methyl oxime was synthesized using clarithromycin A oxime as the raw material by three steps: protection of 2'-OH and 4″-OH with TMS, methylation and de-protection of TMS. The structure was identified by 1H NMR, 13C NMR and HPLC analysis was conducted. Experimental results show that the reactions are greatly affected by catalyst, solvent and pH value. The parameters of HPLC are as follows. The mobile phase is ACN/KH 2PO 4 aqueous solution (V/V=45/55), wavelength is 210 nm, temperature is 30°C and the velocity of flow is 1.0 mL/min. This synthesized compound is of benefit to control the commercial production of clarithromycin.

AB - To control the commercial production of clarithromycin, clarithromycin A(E)9-O-methyl oxime was synthesized using clarithromycin A oxime as the raw material by three steps: protection of 2'-OH and 4″-OH with TMS, methylation and de-protection of TMS. The structure was identified by 1H NMR, 13C NMR and HPLC analysis was conducted. Experimental results show that the reactions are greatly affected by catalyst, solvent and pH value. The parameters of HPLC are as follows. The mobile phase is ACN/KH 2PO 4 aqueous solution (V/V=45/55), wavelength is 210 nm, temperature is 30°C and the velocity of flow is 1.0 mL/min. This synthesized compound is of benefit to control the commercial production of clarithromycin.

KW - Clarithromycin A

KW - Clarithromycin A 9 oxime

KW - Clarithromycin A(E)-9-O-methyl oxime

UR - http://www.scopus.com/inward/record.url?scp=84863291761&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:84863291761

SN - 1001-0645

VL - 32

SP - 102

EP - 105

JO - Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology

JF - Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology

IS - 1

ER -

Synthesis and separation of the clarithromycin A(E)-9-O-methyl oxime

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