ent-7-oxostaurosporine | 174291-07-7

• 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: ent-7-oxostaurosporine
• 英文别名: (2R,3S,4S,6S)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaene-16,18-dione
• CAS: 174291-07-7
• 化学式: C₂₈H₂₄N₄O₄
• 分子量: 480.523
• InChiKey: POTTVLREWUNNRO-XCXUBNKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ent-7-oxostaurosporine 在 sodium tetrahydroborate 、 苯硒酚 、 对甲苯磺酸 作用下， 生成 staurosporine 、 ent-7-oxostaurosporine
  参考文献：
  名称：

  First Total Synthesis of Staurosporine and ent-Staurosporine

  摘要：

  DOI：

  10.1021/ja00106a072
• 作为产物：
  描述：

  3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine 在 palladium dihydroxide 、 氢气 、 sodium methylate 、 sodium hydride 、 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 ent-7-oxostaurosporine
  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

• 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.
• 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