2-[(2R,3S,4S)-4-Acetoxy-5-((2R,4R,6S)-6-cyano-3,3-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl)-2-hydroxy-3-methyl-pentyl]-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-benzoic acid methyl ester | 869964-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(2R,3S,4S)-4-Acetoxy-5-((2R,4R,6S)-6-cyano-3,3-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl)-2-hydroxy-3-methyl-pentyl]-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-benzoic acid methyl ester
• CAS: 869964-32-9
• 化学式: C₄₃H₇₇NO₉Si₃
• 分子量: 836.342
• InChiKey: OOPGLQBOXLHWTO-JTVOMDCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.51
• 重原子数：
  56.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  133.54
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-[(2R,3S,4S)-4-Acetoxy-5-((2R,4R,6S)-6-cyano-3,3-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl)-2-hydroxy-3-methyl-pentyl]-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-benzoic acid methyl ester 在 四丁基氟化铵 、 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 6-[3-(6,8-dihydroxy-5-methyl-1-oxoisochroman-3-yl)-2-hydroxybutyl]-4-hydroxy-5,5-dimethyl-tetrahydropyran-2-carbonitrile
  参考文献：
  名称：

  Concise and Stereoselective Synthesis of the N₇−C₂₅ Fragment of Psymberin

  摘要：

  The N-7-C-25 fragment of the potent and selective cytotoxic agent psymberin has been prepared through a short (12 linear steps, 15 total steps) and stereoselective sequence. Highlights of this route include a very rapid construction of the pentasubstituted arene, a substrate-controlled diastereoselective fragment coupling using a Mukaiyama aldol reaction, and an efficient entry into a key tetrahydropyranyl cyanide.

  DOI：

  10.1021/ol0520267
• 作为产物：
  描述：

  (2R,3R,4S,6R,8S)-4,6-bis-tert-butyldimethylsilanyloxy-2-(2-tert-butyldimethylsilanyloxy-4,6-dihydroxy-3,7,7-trimethyl-8-triethylsilanyloxyundec-10-enyl)-3-methylbenzoic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 2-[(2R,3S,4S)-4-Acetoxy-5-((2R,4R,6S)-6-cyano-3,3-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl)-2-hydroxy-3-methyl-pentyl]-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-benzoic acid methyl ester
  参考文献：
  名称：

  Concise and Stereoselective Synthesis of the N₇−C₂₅ Fragment of Psymberin

  摘要：

  The N-7-C-25 fragment of the potent and selective cytotoxic agent psymberin has been prepared through a short (12 linear steps, 15 total steps) and stereoselective sequence. Highlights of this route include a very rapid construction of the pentasubstituted arene, a substrate-controlled diastereoselective fragment coupling using a Mukaiyama aldol reaction, and an efficient entry into a key tetrahydropyranyl cyanide.

  DOI：

  10.1021/ol0520267