(1S,2S,3R,7R,8R,9E,11E,14R,16R)-7-ethyl-3-hydroxy-8-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-2,10,14-trimethyl-6,19-dioxabicyclo[14.3.0]nonadeca-9,11-diene-5,13-dione | 91661-81-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1S,2S,3R,7R,8R,9E,11E,14R,16R)-7-ethyl-3-hydroxy-8-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-2,10,14-trimethyl-6,19-dioxabicyclo[14.3.0]nonadeca-9,11-diene-5,13-dione
• CAS: 91661-81-3
• 化学式: C₃₁H₅₀O₁₀
• 分子量: 582.732
• InChiKey: LWRJNIIJGWPGTQ-ADIANQOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  泰乐菌素 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 4 A molecular sieve 、 sodium fluoride 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 123.5h， 生成 (1S,2S,3R,7R,8R,9E,11E,14R,16R)-7-ethyl-3-hydroxy-8-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-2,10,14-trimethyl-6,19-dioxabicyclo[14.3.0]nonadeca-9,11-diene-5,13-dione
  参考文献：
  名称：

  Synthesis and evaluation of tylosin-related macrolides modified at the aldehyde function: a new series of orally effective antibiotics

  摘要：

  Modification of the aldehyde group in tylosin and related macrolide antibiotics dramatically enhanced the oral efficacy of the derivatives against experimental infections caused by susceptible bacteria in laboratory animals. A large number and wide variety of aldehyde-modified macrolide derivatives were prepared, utilizing the Mitsunobu reaction and other chemical transformations. Evaluation of in vitro and in vivo antimicrobial activity indicated that derivatives of demycarosyltylosin (desmycosin) combined the broadest spectrum of antimicrobial activity with the best efficacy and bioavailability after oral administration.

  DOI：

  10.1021/jm00403a025

文献信息

• KIRST, HERBERT A.;TOTH, JOHN E.;DEBONO, MANUEL;WILLARD, KEVIN E.;TRUEDELL+, J. MED. CHEM., 31,(1988) N 8, C. 1631-1641
  作者：KIRST, HERBERT A.、TOTH, JOHN E.、DEBONO, MANUEL、WILLARD, KEVIN E.、TRUEDELL+

  DOI：——

  日期：——
• Synthesis and evaluation of tylosin-related macrolides modified at the aldehyde function: a new series of orally effective antibiotics
  作者：Herbert A. Kirst、John E. Toth、Manuel Debono、Kevin E. Willard、Brenda A. Truedell、John L. Ott、Fred T. Counter、Anna M. Felty-Duckworth、Robert S. Pekarek

  DOI：10.1021/jm00403a025

  日期：1988.8

  Modification of the aldehyde group in tylosin and related macrolide antibiotics dramatically enhanced the oral efficacy of the derivatives against experimental infections caused by susceptible bacteria in laboratory animals. A large number and wide variety of aldehyde-modified macrolide derivatives were prepared, utilizing the Mitsunobu reaction and other chemical transformations. Evaluation of in vitro and in vivo antimicrobial activity indicated that derivatives of demycarosyltylosin (desmycosin) combined the broadest spectrum of antimicrobial activity with the best efficacy and bioavailability after oral administration.