(5R,6S)-4-methoxy-5-(4-methoxybenzyloxy)-6-(1-phenylethyl)-5,6-dihydro-2H-pyran-2-one | 259142-63-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 卡瓦内酯
• 英文名称: (5R,6S)-4-methoxy-5-(4-methoxybenzyloxy)-6-(1-phenylethyl)-5,6-dihydro-2H-pyran-2-one
• 英文别名: (5R,6S)-4-methoxy-5-(4-methoxybenzyloxy)-6-phenethyl-5,6-dihydro-2H-pyran-2-one；(2S,3R)-4-methoxy-3-[(4-methoxyphenyl)methoxy]-2-(2-phenylethyl)-2,3-dihydropyran-6-one
• CAS: 259142-63-7
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: BPIBTEMXERMGNY-SIKLNZKXSA-N

物化性质

• 沸点：
  560.3±50.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R,6S)-4-methoxy-5-(4-methoxybenzyloxy)-6-(1-phenylethyl)-5,6-dihydro-2H-pyran-2-one 在 phosphate buffer 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 以92%的产率得到(+)-dihydrokawain-5-ol
  参考文献：
  名称：

  Facile One-Step Synthesis of β-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group:  Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol

  摘要：

  We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from alpha-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a alpha,beta-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a delta-lactone, which was converted into the target compounds in two steps.

  DOI：

  10.1021/jo049858n
• 作为产物：
  描述：

  在 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 生成 (5R,6S)-4-methoxy-5-(4-methoxybenzyloxy)-6-(1-phenylethyl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Facile One-Step Synthesis of β-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group:  Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol

  摘要：

  We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from alpha-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a alpha,beta-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a delta-lactone, which was converted into the target compounds in two steps.

  DOI：

  10.1021/jo049858n

文献信息

• Asymmetric Synthesis of (+)-Dihydrokawain-5-ol
  作者：Yoshitsugu Arai、Tsutomu Masuda、Shinya Yoneda、Yukio Masaki、Motoo Shiro

  DOI：10.1021/jo991307n

  日期：2000.1.1
• Facile One-Step Synthesis of β-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group:  Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol
  作者：Ravi P. Singh、Vinod K. Singh

  DOI：10.1021/jo049858n

  日期：2004.5.1

  We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from alpha-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a alpha,beta-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a delta-lactone, which was converted into the target compounds in two steps.