(S)-(-) methyl α-(3,4,5-trimethoxybenzyl)hemisuccinate | 133269-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-(-) methyl α-(3,4,5-trimethoxybenzyl)hemisuccinate
• 英文别名: (S)-3-methoxycarbonyl-4-(3,4,5-trimethoxy-phenyl)butanoic acid；(3S)-4-methoxy-4-oxo-3-[(3,4,5-trimethoxyphenyl)methyl]butanoic acid
• CAS: 133269-68-8
• 化学式: C₁₅H₂₀O₇
• 分子量: 312.32
• InChiKey: MDPASBRYOIFVSQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-(-) methyl α-(3,4,5-trimethoxybenzyl)hemisuccinate 在 氢氧化钾 、 sodium tetrahydroborate 、 calcium chloride 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (S)-(E)-2-<5-(2-methoxyethoxy)methoxy-3,4-dimethoxybenzylidene>-3-(3,4,5-trimethoxybenzyl)butanolide
  参考文献：
  名称：

  五味子素代谢物的总合成

  摘要：

  实现了五味子素代谢物的总合成。通过相应的3-苄基-1-亚苄基丁内酯的氧化偶合反应，以光学纯净的形式制备了四环内酯中间体（13a-e）。Mukaiyama水合13b提供了羟基内酯（14），将其转化为SZ-M3（4）。通过连续的双键迁移到15a-e，将内酯环还原成烯丙基二醇（32a-e）和连续的双键迁移，引入了代谢物（4-11）常见的C6,7-二醇部分。乙二醇的形成。然后，甲磺酸酯33的还原完成了代谢物的合成。

  DOI：

  10.1016/0040-4020(95)00702-a
• 作为产物：
  描述：

  (+/-)-4-(3,4,5-trimethoxyphenyl)-3-methoxycarbonylbutanoic acid 生成 (S)-(-) methyl α-(3,4,5-trimethoxybenzyl)hemisuccinate
  参考文献：
  名称：

  Resolving Agents. I. (R)-(-)-2-Amino-1-benzyloxybutane, a New Base for the Resolution of Racemic Acids

  摘要：

  Treatment of the readily available (R)-(-) enantiomer of 2-aminobutan-1-ol 1 with sodium hydride followed by benzyl chloride afforded the ($) under bar O-benzyl base (R)-(-)-2. The latter was successfully used for the resolution of racemic alpha-methylsuccinic and alpha-bromosuccinic acids, as well as of the racemic alpha-benzylhemisuccinic esters 8 and 9 respectively.

  DOI：

  10.1080/00397919408011187

文献信息

• Synthesis of Optically Pure Gomisi Lignans: The Total Synthesis of (+)-Schizandrin, (+)-Gomisin A, and (+)-Isoschizandrin in Naturally Occurring Forms
  作者：Masahide Tanaka、Chieko Mukaiyama、Hiroshi Mitsuhashi、Masao Maruno、Takeshi Wakamatsu

  DOI：10.1021/jo00119a010

  日期：1995.7

  The total syntheses of (+)-schizandrin (1), (+)-gomisin A (2), and (+)-isoschizandrin (3) having natural configurations were accomplished. Optically pure butyrolactones ((-)-9, (-)-31) were transformed to alpha-benzylidenebutyrolactones ((+)-10, (+)-32, (+)-35). By a highly efficient iron(III) perchlorate-mediated oxidative coupling reaction of 10, 32, and 35, the key intermediates with biphenyl skeletons ((-)-11, (-)-33) were constructed with high stereoselectivity. Several methods for the stereoselective introduction of the C6-hydroxyl group were examined. For the synthesis of schizandrin and gomisin A, the Mukaiyama hydration reaction of(-)-11 and (-)-33 provided the desired products with satisfactory selectivity. For the synthesis of isoschizandrin, the stereoselective epoxidation of allylic alcohol (+)-48 was successfully utilized taking advantage of its conformational features.