Toluene-4-sulfonic acid (S)-2-hydroxy-2-(4-methoxy-3-triisopropylsilanyloxy-phenyl)-ethyl ester | 179260-99-2

• 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: Toluene-4-sulfonic acid (S)-2-hydroxy-2-(4-methoxy-3-triisopropylsilanyloxy-phenyl)-ethyl ester
• 英文别名: [(2S)-2-hydroxy-2-[4-methoxy-3-tri(propan-2-yl)silyloxyphenyl]ethyl] 4-methylbenzenesulfonate
• CAS: 179260-99-2
• 化学式: C₂₅H₃₈O₆SSi
• 分子量: 494.725
• InChiKey: GCYCCJDDMOZEKH-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (S)-2-hydroxy-2-(4-methoxy-3-triisopropylsilanyloxy-phenyl)-ethyl ester 在 sodium hydroxide 、 正丁基锂 、 四丁基氟化铵 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 白花前胡甲素
  参考文献：
  名称：

  Highly Enantioselective Synthesis of Natural Phyllodulcin

  摘要：

  (S)-[4-Methoxy-3-[(triisopropylsilyl)oxy]phenyl)oxirane (prepared from isovanillin by consecutive silylation, olefination, Sharpless asymmetric cis-dihydroxylation, and dehydration) reacted with [3-(methoxymethoxy)phenyl]lithium (prepared from 3-bromophenol by consecutive methoxymethylation and bromine - lithium exchange) to yield (R)-1-[4-methoxy-3-[(triisopropylsilyl)oxy]phenyl)-2-[3-(methoxymethoxy)phenyl] ethanol. The last compound underwent selective hydrogen-metal exchange with excess of butyllithium affording (after carbonation, lactonization, and deprotection of phenolic groups) the title compound [(R)-3,4-dihydro-8-hydroxy-3-(4-methoxy-3-hydroxyphenyl)-isocoumarin].

  DOI：

  10.1021/jo9603385
• 作为产物：
  描述：

  三异丙基氯硅烷 在 吡啶 、 咪唑 、 AD-mix-α 、 正丁基锂 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 37.25h， 生成 Toluene-4-sulfonic acid (S)-2-hydroxy-2-(4-methoxy-3-triisopropylsilanyloxy-phenyl)-ethyl ester
  参考文献：
  名称：

  Highly Enantioselective Synthesis of Natural Phyllodulcin

  摘要：

  (S)-[4-Methoxy-3-[(triisopropylsilyl)oxy]phenyl)oxirane (prepared from isovanillin by consecutive silylation, olefination, Sharpless asymmetric cis-dihydroxylation, and dehydration) reacted with [3-(methoxymethoxy)phenyl]lithium (prepared from 3-bromophenol by consecutive methoxymethylation and bromine - lithium exchange) to yield (R)-1-[4-methoxy-3-[(triisopropylsilyl)oxy]phenyl)-2-[3-(methoxymethoxy)phenyl] ethanol. The last compound underwent selective hydrogen-metal exchange with excess of butyllithium affording (after carbonation, lactonization, and deprotection of phenolic groups) the title compound [(R)-3,4-dihydro-8-hydroxy-3-(4-methoxy-3-hydroxyphenyl)-isocoumarin].

  DOI：

  10.1021/jo9603385

文献信息

• Highly Enantioselective Synthesis of Natural Phyllodulcin
  作者：Alessio Ramacciotti、Rita Fiaschi、Elio Napolitano

  DOI：10.1021/jo9603385

  日期：1996.1.1

  (S)-[4-Methoxy-3-[(triisopropylsilyl)oxy]phenyl)oxirane (prepared from isovanillin by consecutive silylation, olefination, Sharpless asymmetric cis-dihydroxylation, and dehydration) reacted with [3-(methoxymethoxy)phenyl]lithium (prepared from 3-bromophenol by consecutive methoxymethylation and bromine - lithium exchange) to yield (R)-1-[4-methoxy-3-[(triisopropylsilyl)oxy]phenyl)-2-[3-(methoxymethoxy)phenyl] ethanol. The last compound underwent selective hydrogen-metal exchange with excess of butyllithium affording (after carbonation, lactonization, and deprotection of phenolic groups) the title compound [(R)-3,4-dihydro-8-hydroxy-3-(4-methoxy-3-hydroxyphenyl)-isocoumarin].