(9Z,11E)-(4R,6R,8R)-17,19-Bis-(tert-butyl-dimethyl-silanyloxy)-12-hydroxymethyl-4-methyl-3,7-dioxa-tricyclo[13.4.0.0^6,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione | 140480-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (9Z,11E)-(4R,6R,8R)-17,19-Bis-(tert-butyl-dimethyl-silanyloxy)-12-hydroxymethyl-4-methyl-3,7-dioxa-tricyclo[13.4.0.0^6,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione
• CAS: 140480-14-4
• 化学式: C₃₁H₄₈O₇Si₂
• 分子量: 588.889
• InChiKey: JESLDFFZVRMRRO-KWVIJOQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  40.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  94.59
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (E)-(4R,6R,8S)-17,19-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-4-methyl-3,7-dioxa-tricyclo[13.4.0.0^6,8]nonadeca-1(19),10,15,17-tetraene-2,13-dione 在 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 以30%的产率得到(4R,6R,8R,9Z,11E)-17,19-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione
  参考文献：
  名称：

  Monocillin I和Monorden（或Radicicol）的聚合立体定向全合成

  摘要：

  抗真菌间苯二酚大环内酯类Monocillin I和Monorden（或Radicicol）的第一个总合成已通过收敛的立体定向途径实现。发现TBDMS酚醚适用于所有方案，并在温和的条件下（硼砂/ THF /甲醇水溶液）在最终步骤中除去，因此能够以高收率得到天然大环内酯类，而没有降解。还报道了将双-OTBMDS Monocillin I有效转化为莫诺登。

  DOI：

  10.1016/s0040-4039(00)77713-6

文献信息

• Convergent stereospecific total synthesis of monocillin I and radicicol: some simplifications and improvements
  作者：Isabelle Tichkowsky、Robert Lett

  DOI：10.1016/s0040-4039(02)00713-x

  日期：2002.5

  A much improved and reliable access to the macrolide 9, key-intermediate in our synthesis of monocillin I and radicicol is reported, via a modification of our first synthesis. The formation of the conjugated E.Z-dienone trans-epoxide is now achieved in a much higher yield, in a stereospecific reaction, by elimination of the methanesulfonate ester of the 6'-OH of the intermediate macrolide. It is also shown that the configuration of the 6'-OH has no significant incidence on all the steps leading to 9, and that consequently the two diastereoisomers 12, epimeric at 6', can be used for the synthesis of radicicol. (C) 2002 Elsevier Science Ltd. All rights reserved.