6-hydroxymethyl-5,7-dihydro-12,13-(6-azido-6-deoxy-β-D-mannopyranose-1,2-diyl)pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione | 862778-85-6

• 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: 6-hydroxymethyl-5,7-dihydro-12,13-(6-azido-6-deoxy-β-D-mannopyranose-1,2-diyl)pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
• CAS: 862778-85-6
• 化学式: C₂₆H₁₉N₇O₆
• 分子量: 525.48
• InChiKey: YSXBIBAMYGASBD-LMAIIVCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  39.0
• 可旋转键数：
  3.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  178.81
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6-hydroxymethyl-5,7-dihydro-12,13-(6-azido-6-deoxy-β-D-mannopyranose-1,2-diyl)pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以77%的产率得到12,13-(6-azido-6-deoxy-β-D-mannopyranose-1,2-diyl)-6H-pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
  参考文献：
  名称：

  Synthesis of bridged aza-rebeccamycin analogues

  摘要：

  The syntheses of rebeccamycin analogues possessing a 7-azaindole moiety instead of an indole unit, and with both indole and azaindole moieties linked to the carbohydrate are described. In these bridged aza compounds, the oxygen of the pyranose heterocycle is oriented towards either the indole, or the azaindole unit. In these series, compounds bearing a free imide nitrogen were synthesized by coupling the corresponding aglycones with a sugar pre-tosylated in 2-position via a Mitsunobu reaction. To obtain a precursor for bridged aza-rebeccamycin analogues substituted in 6-position on the sugar moiety, a 2,6-ditosylated sugar was used. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.043
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-6-[12,14-dioxo-13-(phenylmethoxymethyl)-3,5,13,23-tetrazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17,19,21-nonaen-23-yl]-5-(4-methylphenyl)sulfonyloxy-3,4-bis(phenylmethoxy)oxan-2-yl]methyl 4-methylbenzenesulfonate 在 sodium azide 、 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 168.0h， 生成 6-hydroxymethyl-5,7-dihydro-12,13-(6-azido-6-deoxy-β-D-mannopyranose-1,2-diyl)pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
  参考文献：
  名称：

  Synthesis of bridged aza-rebeccamycin analogues

  摘要：

  The syntheses of rebeccamycin analogues possessing a 7-azaindole moiety instead of an indole unit, and with both indole and azaindole moieties linked to the carbohydrate are described. In these bridged aza compounds, the oxygen of the pyranose heterocycle is oriented towards either the indole, or the azaindole unit. In these series, compounds bearing a free imide nitrogen were synthesized by coupling the corresponding aglycones with a sugar pre-tosylated in 2-position via a Mitsunobu reaction. To obtain a precursor for bridged aza-rebeccamycin analogues substituted in 6-position on the sugar moiety, a 2,6-ditosylated sugar was used. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.043