2-[4-acetoxy-5-(6-acetoxy-3,3-dimethyl-4-triethylsilanyloxytetrahydropyran-2-yl)-2-tert-butyldimethylsilanyloxy-3-methylpentyl]-4,6-bis-tert-butyldimethylsilanyloxy-3-methylbenzoic acid methyl ester | 869964-29-4

• 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-5-(6-acetoxy-3,3-dimethyl-4-triethylsilanyloxytetrahydropyran-2-yl)-2-tert-butyldimethylsilanyloxy-3-methylpentyl]-4,6-bis-tert-butyldimethylsilanyloxy-3-methylbenzoic acid methyl ester
• 英文别名: methyl 2-[(2R,3R,4S)-4-acetyloxy-5-[(2R,4R)-6-acetyloxy-3,3-dimethyl-4-triethylsilyloxyoxan-2-yl]-2-[tert-butyl(dimethyl)silyl]oxy-3-methylpentyl]-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methylbenzoate
• CAS: 869964-29-4
• 化学式: C₅₀H₉₄O₁₁Si₄
• 分子量: 983.632
• InChiKey: OECRYCLGHCIBKZ-GDAHQJRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.54
• 重原子数：
  65
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  2-[4-acetoxy-5-(6-acetoxy-3,3-dimethyl-4-triethylsilanyloxytetrahydropyran-2-yl)-2-tert-butyldimethylsilanyloxy-3-methylpentyl]-4,6-bis-tert-butyldimethylsilanyloxy-3-methylbenzoic acid methyl ester 在 (Me₂PO)2HPt(Me₂POH) 三氟化硼乙醚 、 水 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.67h， 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 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 2-[4-acetoxy-5-(6-acetoxy-3,3-dimethyl-4-triethylsilanyloxytetrahydropyran-2-yl)-2-tert-butyldimethylsilanyloxy-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