1-<(benzyloxy)methyl>-4-bromo-3,4-dihydro-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione | 160256-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-<(benzyloxy)methyl>-4-bromo-3,4-dihydro-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione
• 英文别名: 3-Bromo-1-(phenylmethoxymethyl)-4-[1-(2-trimethylsilylethoxymethyl)indol-3-yl]pyrrole-2,5-dione
• CAS: 160256-36-0
• 化学式: C₂₆H₂₉BrN₂O₄Si
• 分子量: 541.517
• InChiKey: LJCOWGLXXUIBND-UHFFFAOYSA-N

物化性质

• 沸点：
  611.2±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<(benzyloxy)methyl>-4-bromo-3,4-dihydro-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione 在 甲基碘化镁 、 sodium hydride 作用下， 反应 15.0h， 生成 1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Staurosporine and ent-Staurosporine:  The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles¹

  摘要：

  The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.

  DOI：

  10.1021/ja952907g
• 作为产物：
  描述：

  N-benzyloxymethyl-3,4-dibromomaleimide 在 甲基碘化镁 、 sodium hydride 作用下， 反应 2.33h， 生成 1-<(benzyloxy)methyl>-4-bromo-3,4-dihydro-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Staurosporine and ent-Staurosporine:  The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles¹

  摘要：

  The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.

  DOI：

  10.1021/ja952907g

文献信息

• First Total Synthesis of Staurosporine and ent-Staurosporine
  作者：J. T. Link、Subharekha Raghavan、Samuel J. Danishefsky

  DOI：10.1021/ja00106a072

  日期：1995.1
• Staurosporine and <i>ent</i>-Staurosporine:  The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles¹
  作者：J. T. Link、Subharekha Raghavan、Michel Gallant、Samuel J. Danishefsky、T. C. Chou、Lawrence M. Ballas

  DOI：10.1021/ja952907g

  日期：1996.1.1

  The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.