(R)-methyl 2,6-dihydroxy-2-(2-hydroxyethyl)-6-methylheptanoate | 1416253-47-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-methyl 2,6-dihydroxy-2-(2-hydroxyethyl)-6-methylheptanoate
• 英文别名: methyl (2R)-2,6-dihydroxy-2-(2-hydroxyethyl)-6-methylheptanoate
• CAS: 1416253-47-8
• 化学式: C₁₁H₂₂O₅
• 分子量: 234.293
• InChiKey: WOVJVOVIDCYABS-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2,6-dihydroxy-2-(2-hydroxyethyl)-6-methylheptanoate 在 三甲基氯硅烷 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.33h， 生成 (R)-dimethyl 2-hydroxy-2-(4-hydroxy-4-methylpentyl)succinate
  参考文献：
  名称：

  Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine

  摘要：

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.

  DOI：

  10.1021/jo302203g
• 作为产物：
  描述：

  3-(2-(dibenzylamino)-4-hydroxy-4-methylpentylidene)dihydrofuran-2(3H)-one 在 palladium 10% on activated carbon 、 氢气 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 5.0~60.0 ℃ 、413.7 kPa 条件下， 反应 4.17h， 生成 (R)-methyl 2,6-dihydroxy-2-(2-hydroxyethyl)-6-methylheptanoate
  参考文献：
  名称：

  Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine

  摘要：

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.

  DOI：

  10.1021/jo302203g

文献信息

• A Concise and Scalable Formal Synthesis of the Enantiopure Side-Chain Diester of Homoharringtonine
  作者：Moran Sun、Xin Jia、Yaowen Lai、Hua Yang

  DOI：10.3184/174751915x14189228913336

  日期：2015.1

  The enantiopure side-chain diester of homoharringtonine (HHT) has been prepared in 38% overall yield, from cheap L-aspartic acid by a linear sequence of 10 chemical operations (mean yield per step: 91%). The experimental operation in each step is convenient, economic and prone to scale up. About 7–10 g of the side-chain diester of HHT is easily prepared within one week from 5 g of L-aspartic acid.

  通过 10 步线性化学反应（每一步的平均收率为 91%），以廉价的 L-天冬氨酸为原料，制备出了对映体纯度为 38%的高哈林鸟嘌呤（HHT）侧链二酯。每一步的实验操作都非常方便、经济，而且易于推广。5 克 L-天门冬氨酸可在一周内轻松制备出约 7-10 克 HHT 侧链二酯。
• Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine
  作者：Hua Yang、Moran Sun、Shuguang Zhao、Ming Zhu、Yangla Xie、Changling Niu、Chunlin Li

  DOI：10.1021/jo302203g

  日期：2013.1.18

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.