5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-2-O-(trifluoroacetyl)-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)indole | 147624-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-2-O-(trifluoroacetyl)-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)indole
• 英文别名: 5-(Benzyloxy)-4-{[3,4,6-tri-O-benzyl-2-O-(trifluoroacetyl)-β-D-glucopyranosyl]oxy}-3-(trifluoroacetyl)indole；[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[[5-phenylmethoxy-3-(2,2,2-trifluoroacetyl)-1H-indol-4-yl]oxy]oxan-3-yl] 2,2,2-trifluoroacetate
• CAS: 147624-39-3
• 化学式: C₄₆H₃₉F₆NO₉
• 分子量: 863.807
• InChiKey: ADDSSEHVCNRUEI-QWMMSZROSA-N

物化性质

• 沸点：
  845.3±65.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  62
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-2-O-(trifluoroacetyl)-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)indole 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2,2,2-trifluoro-1-[4-[(2S,3R,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-5-phenylmethoxy-1H-indol-3-yl]ethanone
  参考文献：
  名称：

  Total synthesis of (-)-ovatolide

  摘要：

  The total synthesis of (-)-ovatolide (1), a tetracyclic indole-containing beta-glucosyl derivative with an unusual pyrano[2,3-b][1,4]dioxocan-6-one system, is described. The beta-glucosidic linkage arose from regio- and stereocontrolled reaction of a protected 1,2-epoxyglucal derivative with 4-hydroxy-5-(benzyloxy)indole, and a lactonization reaction afforded the central dioxocanone system. An alternative strategy that afforded the tetracyclic framework as a mixture of epimers is also described.

  DOI：

  10.1021/jo00062a034
• 作为产物：
  描述：

  2,3-二苄氧基苯甲醛 在 N-甲基吗啉 、 potassium fluoride 、 sodium hydroxide 、 sodium dithionite 、 15-冠醚-5 、 18-冠醚-6 、 硝酸 、 sodium acetate 、 乙酸酐 、 silica gel 、 铁粉 、 溶剂黄146 、 magnesium bromide 作用下， 以 乙醚 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 30.17h， 生成 5-(Benzyloxy)-4-<(3,4,6-tri-O-benzyl-2-O-(trifluoroacetyl)-β-D-glucopyranosyl)oxy>-3-(trifluoroacetyl)indole
  参考文献：
  名称：

  Total synthesis of (-)-ovatolide

  摘要：

  The total synthesis of (-)-ovatolide (1), a tetracyclic indole-containing beta-glucosyl derivative with an unusual pyrano[2,3-b][1,4]dioxocan-6-one system, is described. The beta-glucosidic linkage arose from regio- and stereocontrolled reaction of a protected 1,2-epoxyglucal derivative with 4-hydroxy-5-(benzyloxy)indole, and a lactonization reaction afforded the central dioxocanone system. An alternative strategy that afforded the tetracyclic framework as a mixture of epimers is also described.

  DOI：

  10.1021/jo00062a034

文献信息

• Total synthesis of (-)-ovatolide
  作者：Antonio Delgado、Jon Clardy

  DOI：10.1021/jo00062a034

  日期：1993.5

  The total synthesis of (-)-ovatolide (1), a tetracyclic indole-containing beta-glucosyl derivative with an unusual pyrano[2,3-b][1,4]dioxocan-6-one system, is described. The beta-glucosidic linkage arose from regio- and stereocontrolled reaction of a protected 1,2-epoxyglucal derivative with 4-hydroxy-5-(benzyloxy)indole, and a lactonization reaction afforded the central dioxocanone system. An alternative strategy that afforded the tetracyclic framework as a mixture of epimers is also described.