2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-ethanol | 725268-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-ethanol
• 英文别名: 2-[(1S,3R,4R)-3,4-bis(phenylmethoxy)cyclohexyl]ethanol
• CAS: 725268-43-9
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: IUZSTCWDVUTJRT-VLCRHTCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-ethanol 在 4-二甲氨基吡啶 、 1-叠氮基乙烷 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 3-((1R,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-propionitrile
  参考文献：
  名称：

  Synthetic studies on antascomicin A: construction of the C18–C34 fragment

  摘要：

  Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of asymmetric alkylation and Sharpless epoxidation as key transformations. Coupling of iodide 2 and sulfone 3 furnished the C18-C34 fragment. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.072
• 作为产物：
  描述：

  2-((4R,5R)-4,5-Bis-benzyloxy-cyclohex-2-enyl)-ethanol 在 sodium acetate 、 对甲苯磺酰肼 作用下， 以 乙二醇二甲醚 为溶剂， 反应 5.0h， 以80%的产率得到2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-ethanol
  参考文献：
  名称：

  Synthetic studies on antascomicin A: construction of the C18–C34 fragment

  摘要：

  Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of asymmetric alkylation and Sharpless epoxidation as key transformations. Coupling of iodide 2 and sulfone 3 furnished the C18-C34 fragment. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.072

文献信息

• Synthetic studies on antascomicin A: construction of the C18–C34 fragment
  作者：Haruhiko Fuwa、Yumiko Okamura、Hideaki Natsugari

  DOI：10.1016/j.tet.2004.04.072

  日期：2004.6

  Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of asymmetric alkylation and Sharpless epoxidation as key transformations. Coupling of iodide 2 and sulfone 3 furnished the C18-C34 fragment. (C) 2004 Elsevier Ltd. All rights reserved.