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首页> 外文期刊>Carbohydrate research >Chemical transformation of tylosin derivatives into neutral macrolides having a 3 '-methoxyl group
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Chemical transformation of tylosin derivatives into neutral macrolides having a 3 '-methoxyl group

机译：泰乐菌素衍生物化学转化为具有3'-甲氧基的中性大环内酯

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This paper describes the chemical transformation of the basic 16-membered macrolides, tylosin derivatives, into neutral macrolides having a 3'-methoxyl group. 2',4'-Di-O-acetyl-3,23-bis(O-tert-butyldimethylsilyl)mycaminosyltylonolide 9,20-bis(ethylene acetal) N-oxide (1b) was treated with Ac2O-pyridine in CH2Cl2 to afford the 3'-ketone 1c and the 3'-N-acetyl-3'-N-demethyl derivative 1d in 67 and 5% yield, respectively. Reduction of 1c with Zn(BH4)(2) gave the 3'-alcohol 1e in 84% yield stereoselectively. O-Methylation of 1e with MeOTf and 2,6-di-tert-butylpyridine gave the 3'-methyl ether 1f in 49% yield in spite of the presence of the adjacent acetoxyl groups. Deprotection of 1f provided the desired neutral macrolide 1g. Similar synthetic routes were also used for transformation of the suitably protected 4'-deoxymycaminosyltylonolide 2b and desmycosin 3c into neutral macrolides having a 3'-methoxyl group. It was found that the mycinose moiety of a neutral macrolide plays an important role in its antimicrobial activity. (C) 1998 Elsevier Science Ltd. All rights reserved. [References: 29]
机译：本文介绍了将基本的16元大环内酯，泰乐菌素衍生物化学转化为具有3'-甲氧基的中性大环内酯的方法。将2'，4'-二-O-乙酰基-3,23-双（O-叔丁基二甲基甲硅烷基）mycaminosyltylonolide 9,20-双（乙缩醛）N-氧化物（1b）用Ac2O-吡啶在CH2Cl2中处理，得到3'-酮1c和3'-N-乙酰基-3'-N-脱甲基衍生物1d的产率分别为67和5％。用Zn（BH4）（2）还原1c产生3'-醇1e，立体选择性产率为84％。尽管存在相邻的乙酰氧基，但用MeOTf和2，6-二叔丁基吡啶进行1e的O-甲基化反应仍能以49％的收率得到3'-甲基醚1f。 1f脱保护得到所需的中性大环内酯1g。类似的合成路线也用于将适当保护的4'-脱氧mycaminosyltylonolide 2b和desmycosin 3c转化为具有3'-甲氧基的中性大环内酯。已发现中性大环内酯的真菌糖部分在其抗菌活性中起重要作用。 （C）1998 Elsevier ScienceLtd。保留所有权利。 [参考：29]

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