(6R,8aR)-6-[[(tert-butyldimethylsilyl)oxy]methyl]tetrahydro-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8(8aH)-trione | 1096711-43-1

• 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: (6R,8aR)-6-[[(tert-butyldimethylsilyl)oxy]methyl]tetrahydro-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8(8aH)-trione
• 英文别名: (6R,8aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-methyl-8a-(2-trimethylsilylethylsulfanyl)-6,7-dihydro-3H-pyrrolo[1,2-a]pyrazine-1,4,8-trione
• CAS: 1096711-43-1
• 化学式: C₃₀H₄₂N₂O₄SSi₂
• 分子量: 582.911
• InChiKey: VPBBEUZPCZFCPS-WVXBCFDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6R,8aR)-6-[[(tert-butyldimethylsilyl)oxy]methyl]tetrahydro-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8(8aH)-trione 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 以100%的产率得到(6R,8S,8aR)-6-[[(tert-butyldimethylsilyl)oxy]methyl]hexahydro-8-hydroxy-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4-dione
  参考文献：
  名称：

  Asymmetric Synthesis of the ABC-Ring System of the Antitumor Antibiotic MPC1001

  摘要：

  trans-4-Hydroxy-L-proline was converted into a tricyclic compound representing three contiguous rings of the anticancer antibiotic MPC1001. The tricyclic model contains the dihydrooxepin and diketopiperazine Subunits, as well as one of the Sulfur atoms of the natural product. The diketopiperazine unit was formed by a new method that involves cyclization of an enolate onto the carbonyl of a phenyl carbamate, and the dihydrooxepin ring was generated by using an acid-induced cyclization of an alcohol onto the beta-carbon of a vinylogous amide.

  DOI：

  10.1021/jo802344t
• 作为产物：
  描述：

  phenyl [2-[(2R)-2-[[(tert-butyldiphenylsilyl)oxy]methyl]-4-oxopyrrolidin-1-yl]-2-oxoethyl]methylcarbamate 在 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.25h， 生成 (6R,8aR)-6-[[(tert-butyldimethylsilyl)oxy]methyl]tetrahydro-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8(8aH)-trione
  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.
• Asymmetric Synthesis of the ABC-Ring System of the Antitumor Antibiotic MPC1001
  作者：Jianbiao Peng、Derrick L. J. Clive

  DOI：10.1021/jo802344t

  日期：2009.1.16

  trans-4-Hydroxy-L-proline was converted into a tricyclic compound representing three contiguous rings of the anticancer antibiotic MPC1001. The tricyclic model contains the dihydrooxepin and diketopiperazine Subunits, as well as one of the Sulfur atoms of the natural product. The diketopiperazine unit was formed by a new method that involves cyclization of an enolate onto the carbonyl of a phenyl carbamate, and the dihydrooxepin ring was generated by using an acid-induced cyclization of an alcohol onto the beta-carbon of a vinylogous amide.