(6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-8-hydroxy-2-methyloctahydropyrrolo[1,2-a]piperazine-1,4-dione | 1366297-64-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-8-hydroxy-2-methyloctahydropyrrolo[1,2-a]piperazine-1,4-dione
• CAS: 1366297-64-4
• 化学式: C₃₂H₄₈N₂O₅SSi₂
• 分子量: 628.981
• InChiKey: FLVSEEIUTLUYCB-YFCBNTRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.31
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-8-hydroxy-2-methyloctahydropyrrolo[1,2-a]piperazine-1,4-dione 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
• 作为产物：
  描述：

  phenyl [2-[(2R)-2-[[(tert-butyldiphenylsilyl)oxy]methyl]-4-oxopyrrolidin-1-yl]-2-oxoethyl]methylcarbamate 在 sodium tetrahydroborate 、 水 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.77h， 生成 (6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-8-hydroxy-2-methyloctahydropyrrolo[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