phenyl((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)-methanone | 20715-27-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)-methanone
• CAS: 20715-27-9
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: MREBUTNLZVITIY-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  phenyl((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)-methanone 在 cerium(III) chloride heptahydrate 、 sodium tetrahydroborate 、 水 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以86%的产率得到(S)-phenyl((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methanol
  参考文献：
  名称：

  Total synthesis of 8-methoxygoniodiol related compounds via chiron approach

  摘要：

  The stereoselective synthesis of 8-methoxygoniodiol related compounds was accomplished by using readily available delta-gluconolactone as a chiral source. The stereoselective addition of an aryl Grignard reagent on an aldehyde, stereoselective reduction of a keto group and regioselective opening of a chiral epoxide by ethyl propiolate are the key steps involved in this synthesis. (c) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.05.034
• 作为产物：
  描述：

  (R)-phenyl((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methanol 在 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以91%的产率得到phenyl((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)-methanone
  参考文献：
  名称：

  Total synthesis of 8-methoxygoniodiol related compounds via chiron approach

  摘要：

  The stereoselective synthesis of 8-methoxygoniodiol related compounds was accomplished by using readily available delta-gluconolactone as a chiral source. The stereoselective addition of an aryl Grignard reagent on an aldehyde, stereoselective reduction of a keto group and regioselective opening of a chiral epoxide by ethyl propiolate are the key steps involved in this synthesis. (c) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.05.034