(E,4R,5S)-trans-4-(3-methyl-1-butenyl)-5-(1-methylethyl)-3-(4-methylphenyl)sulfonyl-2-oxazolidinone | 487059-62-1

• 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: (E,4R,5S)-trans-4-(3-methyl-1-butenyl)-5-(1-methylethyl)-3-(4-methylphenyl)sulfonyl-2-oxazolidinone
• 英文别名: (4R,5S)-4-[(E)-3-methylbut-1-enyl]-3-(4-methylphenyl)sulfonyl-5-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 487059-62-1
• 化学式: C₁₈H₂₅NO₄S
• 分子量: 351.467
• InChiKey: LLLRXIWKRXRIDY-PLFKGVGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,4R,5S)-trans-4-(3-methyl-1-butenyl)-5-(1-methylethyl)-3-(4-methylphenyl)sulfonyl-2-oxazolidinone 在 sodium chlorite 、 sodium dihydrogenphosphate 、 萘 、 双氧水 、 sodium 、 臭氧 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 (4S,5S)-5-Isopropyl-2-oxazolidinone-4-carboxylic acid
  参考文献：
  名称：

  Stereodivergent Approach to β-Hydroxy α-Amino Acids from C₂-Symmetrical Alk-2-yne-1,4-diols

  摘要：

  [GRAPHICS]A new stereodivergent route to erythro- and threo-beta-substituted serines from a common G-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereoselective alkyne reduction to either (Z)- or (E)-olefin allows selection of the stereochemistry of cc-carbon in the final amino acid by using a Pd(0)-catalyzed process. This strategy has been applied to the synthesis of (2S,3S)-3-hydroxyleucine.

  DOI：

  10.1021/ol0270428
• 作为产物：
  描述：

  对甲基苯磺酰异氰酸酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三异丙基亚磷酸酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 (E,4R,5S)-trans-4-(3-methyl-1-butenyl)-5-(1-methylethyl)-3-(4-methylphenyl)sulfonyl-2-oxazolidinone
  参考文献：
  名称：

  Stereodivergent Approach to β-Hydroxy α-Amino Acids from C₂-Symmetrical Alk-2-yne-1,4-diols

  摘要：

  [GRAPHICS]A new stereodivergent route to erythro- and threo-beta-substituted serines from a common G-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereoselective alkyne reduction to either (Z)- or (E)-olefin allows selection of the stereochemistry of cc-carbon in the final amino acid by using a Pd(0)-catalyzed process. This strategy has been applied to the synthesis of (2S,3S)-3-hydroxyleucine.

  DOI：

  10.1021/ol0270428

文献信息

• Stereodivergent Approach to β-Hydroxy α-Amino Acids from <i>C</i>₂-Symmetrical Alk-2-yne-1,4-diols
  作者：Marta Amador、Xavier Ariza、Jordi Garcia、Sara Sevilla

  DOI：10.1021/ol0270428

  日期：2002.12.1

  [GRAPHICS]A new stereodivergent route to erythro- and threo-beta-substituted serines from a common G-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereoselective alkyne reduction to either (Z)- or (E)-olefin allows selection of the stereochemistry of cc-carbon in the final amino acid by using a Pd(0)-catalyzed process. This strategy has been applied to the synthesis of (2S,3S)-3-hydroxyleucine.