(5S,6R,7R,E)-methyl 5,6-bis(benzyloxy)-7-hydroxy-7-phenylhept-2-enoate | 1201895-63-7

• 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: (5S,6R,7R,E)-methyl 5,6-bis(benzyloxy)-7-hydroxy-7-phenylhept-2-enoate
• 英文别名: methyl (E,5S,6R,7R)-7-hydroxy-7-phenyl-5,6-bis(phenylmethoxy)hept-2-enoate
• CAS: 1201895-63-7
• 化学式: C₂₈H₃₀O₅
• 分子量: 446.543
• InChiKey: QJDOSDZCWCERTP-OJPKYESMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S,6R,7R,E)-methyl 5,6-bis(benzyloxy)-7-hydroxy-7-phenylhept-2-enoate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以90%的产率得到methyl 2-((2R,4S,5S,6R)-4,5-bis(benzyloxy)-6-phenyltetrahydro-2H-pyran-2-yl)acetate
  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：

  (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

文献信息

• Asymmetric synthesis of Goniothalesdiol A from (R)-2,3-O-cyclohexylidine glyceraldehyde
  作者：Mallam Venkataiah、Palabindela Somaiah、Gowrisankar Reddipalli、Nitin W. Fadnavis

  DOI：10.1016/j.tetasy.2009.08.005

  日期：2009.10

  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.