(3aR,5R,6R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol | 700870-84-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 700870-84-4
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: LGVDAYBLXLSJJQ-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 在 sodium periodate 、 硫酸 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 (2R,3R)-2-(4-methoxybenzyloxy)-3-formyloxy-5-phenyl-1-pentanal
  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：

  (3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-phenylethyl)-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole 在 palladium on activated charcoal sodium tetrahydroborate 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (3aR,5R,6R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-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