(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 | 869964-27-2

• 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: (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
• 英文别名: methyl 4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(2R,3R,4S,6R,8R)-2-[tert-butyl(dimethyl)silyl]oxy-4,6-dihydroxy-3,7,7-trimethyl-8-triethylsilyloxyundec-10-enyl]-3-methylbenzoate
• CAS: 869964-27-2
• 化学式: C₄₇H₉₂O₈Si₄
• 分子量: 897.585
• InChiKey: ZQZXAFQKFXAMSX-CEEQJTCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.22
• 重原子数：
  59
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R,3R,8S)-4,6-bis-tert-butyldimethylsilanyloxy-2-(2-tert-butyldimethylsilanyloxy-4-hydroxy-3-methyl-6-oxo-8-triethylsilanyloxyundec-10-enyl)-3-methylbenzoic acid methyl ester 在 二乙基甲氧基硼烷 、 sodium tetrahydroborate 、 pH 7 buffer 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 (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
  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

文献信息

• Concise and Stereoselective Synthesis of the N₇−C₂₅ Fragment of Psymberin
  作者：Jason C. Rech、Paul E. Floreancig

  DOI：10.1021/ol0520267

  日期：2005.11.1

  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.