7-(6-azido-1,6-dideoxy-β-D-glucopyranos-1-yl)-1,3,4,6-tetrahydrodipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraone | 877610-70-3

• 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: 7-(6-azido-1,6-dideoxy-β-D-glucopyranos-1-yl)-1,3,4,6-tetrahydrodipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraone
• 英文别名: 19-[(2R,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl]-4,9,19-triazapentacyclo[10.7.0.02,6.07,11.013,18]nonadeca-1,6,11,13,15,17-hexaene-3,5,8,10-tetrone
• CAS: 877610-70-3
• 化学式: C₂₂H₁₆N₆O₈
• 分子量: 492.404
• InChiKey: QHCYUKBPYYLYBT-YXASVTNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  182
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  7-(6-azido-1,6-dideoxy-β-D-glucopyranos-1-yl)-1,3,4,6-tetrahydrodipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraone 在 palladium on activated charcoal 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 23.0h， 生成 7-(6-amino-1,6-dideoxy-β-D-glucopyranos-1-yl)-1,3,4,6-tetrahydrodipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraone hydrochloride
  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：

  2-(benzyloxy)methyl-7-(1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-1,3,3a,3b,4,6,6a,6b-octahydrodipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraone 在 palladium dihydroxide 吡啶 、 四氯化碳 、 manganese(IV) oxide 、 sodium azide 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 20.0~90.0 ℃ 、101.33 kPa 条件下， 反应 164.0h， 生成 7-(6-azido-1,6-dideoxy-β-D-glucopyranos-1-yl)-1,3,4,6-tetrahydrodipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraone
  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

文献信息

• Synthesis of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones bearing a sugar moiety
  作者：Hélène Hénon、Fabrice Anizon、Bruno Pfeiffer、Michelle Prudhomme

  DOI：10.1016/j.tet.2005.10.077

  日期：2006.2

  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.