(1R,2R,3S)-2,3-bis(benzyloxy)-1-phenylhex-5-en-1-ol | 1201895-62-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1R,2R,3S)-2,3-bis(benzyloxy)-1-phenylhex-5-en-1-ol
• 英文别名: (1R,2R,3S)-1-phenyl-2,3-bis(phenylmethoxy)hex-5-en-1-ol
• CAS: 1201895-62-6
• 化学式: C₂₆H₂₈O₃
• 分子量: 388.507
• InChiKey: ZLZWMUKKLRWZCN-NXCFDTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  (1R,2R,3S)-2,3-bis(benzyloxy)-1-phenylhex-5-en-1-ol 、 丙烯酸甲酯（MA） 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以91%的产率得到(5S,6R,7R,E)-methyl 5,6-bis(benzyloxy)-7-hydroxy-7-phenylhept-2-enoate
  参考文献：
  名称：

  Asymmetric synthesis of Goniothalesdiol A from (R)-2,3-O-cyclohexylidine glyceraldehyde

  摘要：

  Goniothalesdiol A 1 has been synthesized from (R)-2,3-O-cyclohexylidine glyceraldehyde with high stereoselectivity and 22% overall yield in 11 simple steps. The key features of the synthetic strategy include the stereocontrolled allylation of (R)-2,3-O-cyclohexylidine glyceraldehydes; the cross-metathesis with a Grubbs's second generation catalyst, and the intramolecular base-catalyzed oxy-Michael addition for the formation of the tetrahydropyran ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.005
• 作为产物：
  描述：

  (2S,3S)-2,3-bis(phenylmethoxy)hex-5-enal 、 苯基溴化镁 在 氯化铵 作用下， 以 乙醚 、 水 为溶剂， 反应 3.0h， 以0.633 g的产率得到(1R,2R,3S)-2,3-bis(benzyloxy)-1-phenylhex-5-en-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of Goniothalesdiol A from (R)-2,3-O-cyclohexylidine glyceraldehyde

  摘要：

  Goniothalesdiol A 1 has been synthesized from (R)-2,3-O-cyclohexylidine glyceraldehyde with high stereoselectivity and 22% overall yield in 11 simple steps. The key features of the synthetic strategy include the stereocontrolled allylation of (R)-2,3-O-cyclohexylidine glyceraldehydes; the cross-metathesis with a Grubbs's second generation catalyst, and the intramolecular base-catalyzed oxy-Michael addition for the formation of the tetrahydropyran ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.005