7,8-dibenzyloxy-6-[3-{(tert-butyldimethylsilanyloxy)(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-yl)-methyl}-4,5-dihydroisoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester | 1315508-04-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 7,8-dibenzyloxy-6-[3-{(tert-butyldimethylsilanyloxy)(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-yl)-methyl}-4,5-dihydroisoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester
• 英文别名: Methyl 6-[3-[[tert-butyl(dimethyl)silyl]oxy-[5,6,8-trimethoxy-3,4-bis(phenylmethoxy)naphthalen-2-yl]methyl]-4,5-dihydro-1,2-oxazol-5-yl]-1-oxo-7,8-bis(phenylmethoxy)isochromene-3-carboxylate
• CAS: 1315508-04-3
• 化学式: C₆₂H₆₃NO₁₃Si
• 分子量: 1058.27
• InChiKey: MLROLXOIAZQEOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.66
• 重原子数：
  77
• 可旋转键数：
  23
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  7,8-dibenzyloxy-6-[3-{(tert-butyldimethylsilanyloxy)(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-yl)-methyl}-4,5-dihydroisoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以43%的产率得到7,8-dibenzyloxy-6-[3-{(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-yl)hydroxymethyl}-4,5-dihydroisoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Alternative Spiroketalization Methods toward Purpuromycin: A Diketone Approach To Prevent Benzofuran Formation

  摘要：

  The central portion of purpuromycin has been assembled via a classical spiroketalization reaction. Key to promoting this reaction mode versus benzofuran formation was the oxidation state of the spiroketal core. With a higher oxidation state, even the electron-deficient isocoumarin found in purpuromycin could be employed directly in the spiroketalization. The two halves of the spiroketalization precursor were joined via a nitrile oxide/styrene 1,3-dipolar cycloaddition. A very mild selenium dioxide oxidation was used to introduce the required oxidation state of the spiroketal core.

  DOI：

  10.1021/jo200399z
• 作为产物：
  描述：

  ethyl 3,4-dihydro-5,6,8-trimethoxy-3,4-dioxonaphthalene-2-carboxylate 在 lithium aluminium tetrahydride 、 正丁基锂 、 sodium dithionite 、 水 、 异氰酸对硝基苯 、 potassium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 90.58h， 生成 7,8-dibenzyloxy-6-[3-{(tert-butyldimethylsilanyloxy)(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-yl)-methyl}-4,5-dihydroisoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Alternative Spiroketalization Methods toward Purpuromycin: A Diketone Approach To Prevent Benzofuran Formation

  摘要：

  The central portion of purpuromycin has been assembled via a classical spiroketalization reaction. Key to promoting this reaction mode versus benzofuran formation was the oxidation state of the spiroketal core. With a higher oxidation state, even the electron-deficient isocoumarin found in purpuromycin could be employed directly in the spiroketalization. The two halves of the spiroketalization precursor were joined via a nitrile oxide/styrene 1,3-dipolar cycloaddition. A very mild selenium dioxide oxidation was used to introduce the required oxidation state of the spiroketal core.

  DOI：

  10.1021/jo200399z

文献信息

• Alternative Spiroketalization Methods toward Purpuromycin: A Diketone Approach To Prevent Benzofuran Formation
  作者：Andrew N. Lowell、Michael W. Fennie、Marisa C. Kozlowski

  DOI：10.1021/jo200399z

  日期：2011.8.19

  The central portion of purpuromycin has been assembled via a classical spiroketalization reaction. Key to promoting this reaction mode versus benzofuran formation was the oxidation state of the spiroketal core. With a higher oxidation state, even the electron-deficient isocoumarin found in purpuromycin could be employed directly in the spiroketalization. The two halves of the spiroketalization precursor were joined via a nitrile oxide/styrene 1,3-dipolar cycloaddition. A very mild selenium dioxide oxidation was used to introduce the required oxidation state of the spiroketal core.