A new convenient transformation of erythromycin A into clarithromycin

被引：9

作者：

Allevi, P ^{[1
]}

Longo, A ^{[1
]}

Anastasia, M ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Chim & Biochem Med, I-20133 Milan, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 1999年 / 7卷 / 12期

关键词：

antibiotics; antibacterials; clarithromycin; erythromycin A; methylation;

D O I：

10.1016/S0968-0896(99)00230-8

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Erythromycin A was transformed into clarithromycin by the sequence of reactions: selective thexyldimethylsilylation of the 9-oxime, trimethylsilylation of the 2',4 "-hydroxy groups, methylation of the resulting 2',4 "-[O-bis(trimethylsilyl)]-9-[O-(dimethylthexylsilyl)oxime] and acidic regeneration of the protected functionalities. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2749 / 2752

页数：4

相关论文

共 12 条

[1] KINETIC-STUDIES ON THE DECOMPOSITION OF ERYTHROMYCIN-A IN AQUEOUS ACIDIC AND NEUTRAL BUFFERS [J].

ATKINS, PJ ;

HERBERT, TO ;

JONES, NB .

INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1986, 30 (2-3) :199-207

[2]

Bryskier A.J., 1993, Macrolides: chemistry, pharmacology and clinical uses

[3] AN ANALYSIS OF THE H-1 AND C-13 NMR-SPECTRA OF ERYTHROMYCIN-A USING TWO-DIMENSIONAL METHODS [J].

EVERETT, JR ;

TYLER, JW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2599-2603

[4] ACID DEGRADATION OF ERYTHROMYCIN-A AND ERYTHROMYCIN-B [J].

KURATH, P ;

JONES, PH ;

EGAN, RS ;

PERUN, TJ .

EXPERIENTIA, 1971, 27 (04) :362-&

[5] CHEMICAL MODIFICATION OF ERYTHROMYCINS .1. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 6-O-METHYLERYTHROMYCINS-A [J].

MORIMOTO, S ;

TAKAHASHI, Y ;

WATANABE, Y ;

OMURA, S .

JOURNAL OF ANTIBIOTICS, 1984, 37 (02) :187-189

[6] CHEMICAL MODIFICATION OF ERYTHROMYCINS .2. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF O-ALKYL DERIVATIVES OF ERYTHROMYCIN-A [J].

MORIMOTO, S ;

MISAWA, Y ;

ADACHI, T ;

NAGATE, T ;

WATANABE, Y ;

OMURA, S .

JOURNAL OF ANTIBIOTICS, 1990, 43 (03) :286-294

[7] CHEMICAL MODIFICATION OF ERYTHROMYCINS .3. INVITRO AND INVIVO ANTIBACTERIAL ACTIVITIES OF NEW SEMISYNTHETIC 6-O-METHYLERYTHROMYCINS-A, TE-031 (CLARITHROMYCIN) AND TE-032 [J].

MORIMOTO, S ;

NAGATE, T ;

SUGITA, K ;

ONO, T ;

NUMATA, K ;

MIYACHI, J ;

MISAWA, Y ;

YAMADA, K ;

OMURA, S .

JOURNAL OF ANTIBIOTICS, 1990, 43 (03) :295-305

[8] THE CONFORMATION OF 6-METHOXYERYTHROMYCIN-A IN WATER DETERMINED BY PROTON NMR-SPECTROSCOPY [J].

STEINMETZ, WE ;

BERSCH, R ;

TOWSON, J ;

PESIRI, D .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (26) :4842-4845

[9] CHEMICAL MODIFICATION OF ERYTHROMYCINS .9. SELECTIVE METHYLATION AT THE C-6 HYDROXYL GROUP OF ERYTHROMYCIN-A OXIME DERIVATIVES AND PREPARATION OF CLARITHROMYCIN [J].

WATANABE, Y ;

MORIMOTO, S ;

ADACHI, T ;

KASHIMURA, M ;

ASAKA, T .

JOURNAL OF ANTIBIOTICS, 1993, 46 (04) :647-660

[10] CHEMICAL MODIFICATION OF ERYTHROMYCINS .12. A FACILE SYNTHESIS OF CLARITHROMYCIN (6-O-METHYLERYTHROMYCIN A) VIA 2'-SILYLETHERS OF ERYTHROMYCIN A DERIVATIVES [J].

WATANABE, Y ;

ADACHI, T ;

ASAKA, T ;

KASHIMURA, M ;

MATSUNAGA, T ;

MORIMOTO, S .

JOURNAL OF ANTIBIOTICS, 1993, 46 (07) :1163-1167