2-((2S,3S,E)-4-(1-(benzyldimethylsilyl)ethylidene)-2-(methoxycarbonyl)-1-tosylpyrrolidin-3-yl)acetic acid | 1259286-29-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-((2S,3S,E)-4-(1-(benzyldimethylsilyl)ethylidene)-2-(methoxycarbonyl)-1-tosylpyrrolidin-3-yl)acetic acid
• CAS: 1259286-29-7
• 化学式: C₂₆H₃₃NO₆SSi
• 分子量: 515.703
• InChiKey: ZZLIXCSEPYDRHR-TXVSASMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  100.98
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-((2S,3S,E)-4-(1-(benzyldimethylsilyl)ethylidene)-2-(methoxycarbonyl)-1-tosylpyrrolidin-3-yl)acetic acid 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.03h， 生成 methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-4-[1-(hydroxydimethylsilyl)ethylidene]-2-methoxycarbonyl-3-pyrrolidineacetate
  参考文献：
  名称：

  Stereocontrolled Total Syntheses of Isodomoic Acids G and H via a Unified Strategy

  摘要：

  Marine neuroexcitatory compounds isodomoic acids G and H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction. Dividing each target compound into the core fragment and the side-chain fragment enabled the synthesis to be convergent. The trans-2,3-disubstituted pyrrolidine core fragment was accessed through a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of a vinylglycine-derived 1,6-enyne. A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.

  DOI：

  10.1021/jo101790z
• 作为产物：
  描述：

  methyl (2S)-2-[[(4-methylphenyl)sulfonyl]-(2-butyn-1-yl)-amino]-4-(phenylseleno)butanoate 在 (acetylacetonato)dicarbonylrhodium (l) 、 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 双氧水 作用下， 以 四氢呋喃 、 水 、 甲苯 、 叔丁醇 为溶剂， 120.0 ℃ 、4.14 MPa 条件下， 反应 29.0h， 生成 2-((2S,3S,E)-4-(1-(benzyldimethylsilyl)ethylidene)-2-(methoxycarbonyl)-1-tosylpyrrolidin-3-yl)acetic acid
  参考文献：
  名称：

  Stereocontrolled Total Syntheses of Isodomoic Acids G and H via a Unified Strategy

  摘要：

  Marine neuroexcitatory compounds isodomoic acids G and H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction. Dividing each target compound into the core fragment and the side-chain fragment enabled the synthesis to be convergent. The trans-2,3-disubstituted pyrrolidine core fragment was accessed through a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of a vinylglycine-derived 1,6-enyne. A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.

  DOI：

  10.1021/jo101790z