[4-[(5S,5aR,8aR,9R)-5-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] benzyl carbonate | 270071-44-8

• 英文名称: [4-[(5S,5aR,8aR,9R)-5-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] benzyl carbonate
• CAS: 270071-44-8
• 化学式: C₄₇H₄₆O₁₁
• 分子量: 786.876
• InChiKey: KRWHVGBTRCOQQZ-FFXURSROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  58
• 可旋转键数：
  10
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [4-[(5S,5aR,8aR,9R)-5-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] benzyl carbonate 反应 3.0h， 以71%的产率得到
  参考文献：
  名称：

  Novel “Reverse Kahne-Type Glycosylation”:  Access to O-, N-, and C-Linked Epipodophyllotoxin Conjugates

  摘要：

  Exposure of epipodophyllotoxin C-4-sulfoxides to triflic anhydride, followed by a silyl glycoside, provides a glycoconjugate of the etoposide variety via formal "reverse Kahne glycosylation," To our knowledge, this is the first example of this variant of the Kahne activation method wherein the activating functionality is positioned on the aglycon, rather than on the sugar. Phenols, anilines, or allyl silanes are also efficiently captured at C-4, producing the corresponding O-, N, and C linked lignan conjugates.

  DOI：

  10.1021/ol005732a
• 作为产物：
  描述：

  4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin 在 三氟化硼乙醚 、 trifluoromethanesulfonic acid anhydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 [4-[(5S,5aR,8aR,9R)-5-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] benzyl carbonate
  参考文献：
  名称：

  Novel “Reverse Kahne-Type Glycosylation”:  Access to O-, N-, and C-Linked Epipodophyllotoxin Conjugates

  摘要：

  Exposure of epipodophyllotoxin C-4-sulfoxides to triflic anhydride, followed by a silyl glycoside, provides a glycoconjugate of the etoposide variety via formal "reverse Kahne glycosylation," To our knowledge, this is the first example of this variant of the Kahne activation method wherein the activating functionality is positioned on the aglycon, rather than on the sugar. Phenols, anilines, or allyl silanes are also efficiently captured at C-4, producing the corresponding O-, N, and C linked lignan conjugates.

  DOI：

  10.1021/ol005732a