| 1571891-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• CAS: 1571891-88-7
• 化学式: C₃₀H₄₄O₆Si
• 分子量: 528.761
• InChiKey: BEMRLRPFNSZZPO-PKIMSIDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 碘 、 戴斯-马丁氧化剂 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.5h， 生成 methyl (S)-5-methoxy-2-[(2S,3S)-3-methyl-5-oxotetrahydrofuran-2-yl]chroman-2-carboxylate
  参考文献：
  名称：

  The Paecilin Puzzle ‒ Enantioselective Synthesis of the Proposed Structures of Paecilin A and B

  摘要：

  For the synthesis of the two diastereomers 3c and 3d of the proposed structure of paecilin B (3) phenol 19, containing an alkenyl moiety, was treated with Pd(II) in the presence of the chiral BOXAX ligand 9b to give 20 with 96% ee. A subsequent Sharpless dihydroxylation afforded two isomeric diols, which were further transfoimed into 31 and 32. The final steps included removal of the silyl protecting group with simultaneous lactone formation, oxidation and cleavage of the methyl ether. For the preparation of the dimeric paecilin A (1) brominated intermediate 38 was treated with (Bpin)(2), S-Phos and Pd(OAc)(2). The spectroscopic data of the new compounds did not match those of the isolated natural products.

  DOI：

  10.3987/com-13-s(s)68
• 作为产物：
  描述：

  (R)-2-((R)-2-((benzyloxy)methyl)-5-methoxychroman-2-yl)-2-((tert-butyldimethylsilyl)oxy)acetaldehyde 在 三甲基氯硅烷 、 copper(I) bromide dimethylsulfide complex 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  The Paecilin Puzzle ‒ Enantioselective Synthesis of the Proposed Structures of Paecilin A and B

  摘要：

  For the synthesis of the two diastereomers 3c and 3d of the proposed structure of paecilin B (3) phenol 19, containing an alkenyl moiety, was treated with Pd(II) in the presence of the chiral BOXAX ligand 9b to give 20 with 96% ee. A subsequent Sharpless dihydroxylation afforded two isomeric diols, which were further transfoimed into 31 and 32. The final steps included removal of the silyl protecting group with simultaneous lactone formation, oxidation and cleavage of the methyl ether. For the preparation of the dimeric paecilin A (1) brominated intermediate 38 was treated with (Bpin)(2), S-Phos and Pd(OAc)(2). The spectroscopic data of the new compounds did not match those of the isolated natural products.

  DOI：

  10.3987/com-13-s(s)68