3-{1-Benzyloxymethyl-4-[1-((3aR,6R,7aR)-1-benzyloxymethyl-4-methylene-2-oxo-hexahydro-pyrano[4,3-d]oxazol-6-yl)-1H-indol-3-yl]-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl}-indole-1-carboxylic acid benzyl ester | 174148-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-{1-Benzyloxymethyl-4-[1-((3aR,6R,7aR)-1-benzyloxymethyl-4-methylene-2-oxo-hexahydro-pyrano[4,3-d]oxazol-6-yl)-1H-indol-3-yl]-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl}-indole-1-carboxylic acid benzyl ester
• CAS: 174148-66-4
• 化学式: C₅₁H₄₂N₄O₉
• 分子量: 854.916
• InChiKey: VFGNRFDLWSRCKX-TXIZUCIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.03
• 重原子数：
  64.0
• 可旋转键数：
  13.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  130.77
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3-{1-Benzyloxymethyl-4-[1-((3aR,6R,7aR)-1-benzyloxymethyl-4-methylene-2-oxo-hexahydro-pyrano[4,3-d]oxazol-6-yl)-1H-indol-3-yl]-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl}-indole-1-carboxylic acid benzyl ester 在 samarium diiodide 、 air 、 potassium tert-butylate 、 碘 、 L-Selectride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  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：

  3-{1-Benzyloxymethyl-4-[1-((3aR,4R,6R,7aR)-1-benzyloxymethyl-4-iodomethyl-2-oxo-hexahydro-pyrano[4,3-d]oxazol-6-yl)-1H-indol-3-yl]-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl}-indole-1-carboxylic acid benzyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到3-{1-Benzyloxymethyl-4-[1-((3aR,6R,7aR)-1-benzyloxymethyl-4-methylene-2-oxo-hexahydro-pyrano[4,3-d]oxazol-6-yl)-1H-indol-3-yl]-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl}-indole-1-carboxylic acid benzyl ester
  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