3-[1-(benzyloxy)methyl-2,5-dioxopyrrolidin-3-yl]-1-(1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-indole | 877610-62-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3-[1-(benzyloxy)methyl-2,5-dioxopyrrolidin-3-yl]-1-(1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-indole
• CAS: 877610-62-3
• 化学式: C₅₄H₅₂N₂O₈
• 分子量: 857.015
• InChiKey: YANBGZQTBNRSJA-MSSYNLFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.53
• 重原子数：
  64.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  97.69
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-[1-(benzyloxy)methyl-2,5-dioxopyrrolidin-3-yl]-1-(1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-indole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以91%的产率得到3-[1-(benzyloxy)methyl-2,5-dihydro-2,5-dioxopyrrol-3-yl]-1-(1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-1H-indole
  参考文献：
  名称：

  Synthesis of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones bearing a sugar moiety

  摘要：

  The synthesis of a series of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones, structurally related to the G2 checkpoint inhibitor granulatimide and bearing a sugar moiety, is described. Substitutions were carried out at the 6-position of the glycosyl unit to lead to an amino substituent as observed in many biologically active compounds such as anthracyclins or staurosporines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.077
• 作为产物：
  描述：

  1-<(benzyloxy)methyl>-4-bromo-3,4-dihydro-3-<1H-indol-3-yl>-1H-pyrrole-2,5-dione 在 palladium on activated charcoal 吡啶 、 偶氮二甲酸二异丙酯 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 3-[1-(benzyloxy)methyl-2,5-dioxopyrrolidin-3-yl]-1-(1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-indole
  参考文献：
  名称：

  Synthesis of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones bearing a sugar moiety

  摘要：

  The synthesis of a series of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones, structurally related to the G2 checkpoint inhibitor granulatimide and bearing a sugar moiety, is described. Substitutions were carried out at the 6-position of the glycosyl unit to lead to an amino substituent as observed in many biologically active compounds such as anthracyclins or staurosporines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.077