1-Benzyloxymethyl-3-[1-((3aR,4R,6R,7aR)-1-benzyloxymethyl-4-iodomethyl-2-oxo-hexahydro-pyrano[4,3-d]oxazol-6-yl)-1H-indol-3-yl]-4-(1H-indol-3-yl)-pyrrole-2,5-dione | 174148-64-2

• 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-Benzyloxymethyl-3-[1-((3aR,4R,6R,7aR)-1-benzyloxymethyl-4-iodomethyl-2-oxo-hexahydro-pyrano[4,3-d]oxazol-6-yl)-1H-indol-3-yl]-4-(1H-indol-3-yl)-pyrrole-2,5-dione
• CAS: 174148-64-2
• 化学式: C₄₃H₃₇IN₄O₇
• 分子量: 848.694
• InChiKey: NULLDCPULUVXBC-MARFHDPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.66
• 重原子数：
  55.0
• 可旋转键数：
  12.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  115.33
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-Benzyloxymethyl-3-[1-((3aR,4R,6R,7aR)-1-benzyloxymethyl-4-iodomethyl-2-oxo-hexahydro-pyrano[4,3-d]oxazol-6-yl)-1H-indol-3-yl]-4-(1H-indol-3-yl)-pyrrole-2,5-dione 在 4-二甲氨基吡啶 、 samarium diiodide 、 TEA 、 L-Selectride 、 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， 生成 (3aR,6R,7aR)-1-Benzyloxymethyl-6-{3-[1-benzyloxymethyl-4-(1H-indol-3-yl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-indol-1-yl}-4-methylene-hexahydro-pyrano[4,3-d]oxazol-2-one
  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：

  1-Benzyloxymethyl-3-[1-((3aR,4S,6R,7aR)-1-benzyloxymethyl-4-hydroxymethyl-2-oxo-hexahydro-pyrano[4,3-d]oxazol-6-yl)-1H-indol-3-yl]-4-(1H-indol-3-yl)-pyrrole-2,5-dione 在 咪唑 、 碘 、 三苯基膦 作用下， 以88%的产率得到1-Benzyloxymethyl-3-[1-((3aR,4R,6R,7aR)-1-benzyloxymethyl-4-iodomethyl-2-oxo-hexahydro-pyrano[4,3-d]oxazol-6-yl)-1H-indol-3-yl]-4-(1H-indol-3-yl)-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