ethyl (3S,6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-2-methyl-1,4-dioxo-8-[(triethylsilyl)oxy]octahydropyrrolo-[1,2-a]piperazine-3-carboxylate | 1366297-71-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (3S,6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-2-methyl-1,4-dioxo-8-[(triethylsilyl)oxy]octahydropyrrolo-[1,2-a]piperazine-3-carboxylate
• 英文别名: ethyl (3S,6R,8S,8aR)-8a-[[tert-butyl(dimethyl)silyl]oxymethylsulfanyl]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-methyl-1,4-dioxo-8-triethylsilyloxy-3,6,7,8-tetrahydropyrrolo[1,2-a]pyrazine-3-carboxylate
• CAS: 1366297-71-3
• 化学式: C₄₁H₆₆N₂O₇SSi₃
• 分子量: 815.307
• InChiKey: BPUNFXOOBKSCMT-KUIFZRJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.37
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (6R)-6-[[(tert-butyldimethylsilyl)oxy]methyl]tetrahydro-2-methylpyrrolo[1,2-a]pyrazine-1,4,8(8aH)-trione 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 水 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.1h， 生成 ethyl (3R,6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-2-methyl-1,4-dioxo-8-[(triethylsilyl)oxy]octahydropyrrolo-[1,2-a]piperazine-3-carboxylate 、 ethyl (3S,6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-2-methyl-1,4-dioxo-8-[(triethylsilyl)oxy]octahydropyrrolo-[1,2-a]piperazine-3-carboxylate
  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

• 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.