(3R,6R,8S,8aR)-3,8a-bis({[(tert-butyldimethylsilyl)oxy]methyl}sulfanyl)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2-methyl-8-[(triethylsilyl)oxy]octahydropyrrolo[1,2-a]piperazine-1,4-dione | 1366297-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,6R,8S,8aR)-3,8a-bis({[(tert-butyldimethylsilyl)oxy]methyl}sulfanyl)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2-methyl-8-[(triethylsilyl)oxy]octahydropyrrolo[1,2-a]piperazine-1,4-dione
• CAS: 1366297-77-9
• 化学式: C₄₅H₇₈N₂O₆S₂Si₄
• 分子量: 919.598
• InChiKey: IBCSIVLDJNAJEO-ZYLMGOAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.47
• 重原子数：
  59.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  77.54
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3R,6R,8S,8aR)-3,8a-bis({[(tert-butyldimethylsilyl)oxy]methyl}sulfanyl)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2-methyl-8-[(triethylsilyl)oxy]octahydropyrrolo[1,2-a]piperazine-1,4-dione 在 四丁基氟化铵 、 溶剂黄146 、 碘 作用下， 生成 (1R,2S,4R,7R)-4-([(tert-butyldiphenylsilyl)oxy]methyl)-2-hydroxy-11-methyl-8,9-dithia-5,11-diazatricyclo[5.2.2.0(1,5)]undecane-6,10-dione
  参考文献：
  名称：

  Reagent for Divalent Sulfur Protection: Preparation of 4-Methylbenzenesulfonothioic Acid, S-[[[(1,1-Dimethylethyl)-Dimethylsilyl]oxy]methyl] Ester

  摘要：

  DOI：

  10.15227/orgsyn.090.0010
• 作为产物：
  描述：

  (tert-butyldimethylsilyloxy)methyl chloride 在 lithium diisopropyl amide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 (3R,6R,8S,8aR)-3,8a-bis({[(tert-butyldimethylsilyl)oxy]methyl}sulfanyl)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2-methyl-8-[(triethylsilyl)oxy]octahydropyrrolo[1,2-a]piperazine-1,4-dione
  参考文献：
  名称：

  Reagent for Divalent Sulfur Protection: Preparation of 4-Methylbenzenesulfonothioic Acid, S-[[[(1,1-Dimethylethyl)-Dimethylsilyl]oxy]methyl] Ester

  摘要：

  DOI：

  10.15227/orgsyn.090.0010

文献信息

• Synthetic studies related to MPC1001: formation of a model epidithiodiketopiperazine
  作者：Lihong Wang、Derrick L.J. Clive

  DOI：10.1016/j.tetlet.2012.01.055

  日期：2012.3

  A tricyclic epidithiodiketopiperazine was prepared having structural features related to the antitumor antibiotic MPC1001. The method is based on the use of the sulfenylating agent p-MeC6H4S(O-2)SCH2OSiMe2Bu-t to introduce two protected sulfur atoms in a sequential and stereocontrolled manner. Fluoride-induced deprotection to remove the CH2OSiMe2Bu-t units and release two sulfhydryl groups, followed by in situ oxidation, then generated the required bridged disulfide. (C) 2012 Elsevier Ltd. All rights reserved.