1-benzyloxymethyl-2,5-dihydro-3-[1-(2-O-tosyl-3,4,6-tri-O-benzyl-β-D-glucopyranos-1-yl)-indol-3-yl]-4-[1-phenylsulfonyl-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione | 862778-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzyloxymethyl-2,5-dihydro-3-[1-(2-O-tosyl-3,4,6-tri-O-benzyl-β-D-glucopyranos-1-yl)-indol-3-yl]-4-[1-phenylsulfonyl-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione
• 英文别名: [(2R,3R,4S,5R,6R)-2-[3-[4-[1-(benzenesulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-2,5-dioxo-1-(phenylmethoxymethyl)pyrrol-3-yl]indol-1-yl]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] 4-methylbenzenesulfonate
• CAS: 862778-71-0
• 化学式: C₆₇H₅₈N₄O₁₂S₂
• 分子量: 1175.35
• InChiKey: KDLWQZUVZHEELD-AGESRLQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.05
• 重原子数：
  85.0
• 可旋转键数：
  22.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  183.79
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  1-benzyloxymethyl-2,5-dihydro-3-[1-(2-O-tosyl-3,4,6-tri-O-benzyl-β-D-glucopyranos-1-yl)-indol-3-yl]-4-[1-phenylsulfonyl-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以81%的产率得到1-benzyloxymethyl-2,5-dihydro-3-[1-(2-O-tosyl-3,4,6-tri-O-benzyl-β-D-glucopyranos-1-yl)-indol-3-yl]-4-[1H-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-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：

  1-O-acetyl-2-O-tosyl-3,4,6-tri-O-benzyl-D-glucopyranose 在 偶氮二甲酸二异丙酯 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 1-benzyloxymethyl-2,5-dihydro-3-[1-(2-O-tosyl-3,4,6-tri-O-benzyl-β-D-glucopyranos-1-yl)-indol-3-yl]-4-[1-phenylsulfonyl-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-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