(6R,8S,8aR)-6-([(tert-butyldiphenylsilyl)oxy]methyl)-2-methyl-8-[(triethylsilyl)oxy]-8a-([(triphenylmethyl)sulfanyl]disulfanyl)octahydropyrrolo[1,2-a]piperazine-1,4-dione | 1366297-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (6R,8S,8aR)-6-([(tert-butyldiphenylsilyl)oxy]methyl)-2-methyl-8-[(triethylsilyl)oxy]-8a-([(triphenylmethyl)sulfanyl]disulfanyl)octahydropyrrolo[1,2-a]piperazine-1,4-dione
• 英文别名: (6R,8S,8aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-methyl-8-triethylsilyloxy-8a-(trityltrisulfanyl)-3,6,7,8-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 1366297-67-7
• 化学式: C₅₀H₆₀N₂O₄S₃Si₂
• 分子量: 905.406
• InChiKey: QUADFMUORZRARQ-YPPXMBQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.74
• 重原子数：
  61
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (6R,8S,8aR)-6-([(tert-butyldiphenylsilyl)oxy]methyl)-2-methyl-8-[(triethylsilyl)oxy]-8a-([(triphenylmethyl)sulfanyl]disulfanyl)octahydropyrrolo[1,2-a]piperazine-1,4-dione
  参考文献：
  名称：

  Synthetic studies related to MPC1001: formation of a model epidithiodiketopiperazine

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2012.01.055

文献信息

• Reagent for Divalent Sulfur Protection: Preparation of 4-Methylbenzenesulfonothioic Acid, S-[[[(1,1-Dimethylethyl)-Dimethylsilyl]oxy]methyl] Ester
  作者：Wang, Lihong、Clive, Derrick L.J.

  DOI：10.15227/orgsyn.090.0010

  日期：——
• 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.