2-[4-acetoxy-2-tert-butyldimethylsilanyloxy-5-(6-cyano-3,3-dimethyl-4-triethylsilanyloxytetrahydropyran-2-yl)-3-methylpentyl]-4,6-bis-tert-butyldimethylsilanyloxy-3-methylbenzoic acid methyl ester | 869964-30-7

• 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-[4-acetoxy-2-tert-butyldimethylsilanyloxy-5-(6-cyano-3,3-dimethyl-4-triethylsilanyloxytetrahydropyran-2-yl)-3-methylpentyl]-4,6-bis-tert-butyldimethylsilanyloxy-3-methylbenzoic acid methyl ester
• CAS: 869964-30-7
• 化学式: C₄₉H₉₁NO₉Si₄
• 分子量: 950.605
• InChiKey: QFAPJTBUPJIESS-SOWNDVOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.54
• 重原子数：
  63.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  122.54
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-[4-acetoxy-2-tert-butyldimethylsilanyloxy-5-(6-cyano-3,3-dimethyl-4-triethylsilanyloxytetrahydropyran-2-yl)-3-methylpentyl]-4,6-bis-tert-butyldimethylsilanyloxy-3-methylbenzoic acid methyl ester 在 (Me₂PO)2HPt(Me₂POH) 水 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2-[4-acetoxy-2-tert-butyldimethylsilanyloxy-5-(6-carbamoyl-3,3-dimethyl-4-triethylsilanyloxytetrahydropyran-2-yl)-3-methylpentyl]-4,6-bis-tert-butyldimethyl-silanyloxy-3-methylbenzoic 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
• 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 、 三氟化硼乙醚 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 14.67h， 生成 2-[4-acetoxy-2-tert-butyldimethylsilanyloxy-5-(6-cyano-3,3-dimethyl-4-triethylsilanyloxytetrahydropyran-2-yl)-3-methylpentyl]-4,6-bis-tert-butyldimethylsilanyloxy-3-methylbenzoic 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