(4R)-4-benzyl-3-[(E,2R,3R,4R,5S)-3,5-dihydroxy-2,4-dimethyl-7-phenylhept-6-enoyl]-1,3-oxazolidin-2-one | 1041202-02-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (4R)-4-benzyl-3-[(E,2R,3R,4R,5S)-3,5-dihydroxy-2,4-dimethyl-7-phenylhept-6-enoyl]-1,3-oxazolidin-2-one
• CAS: 1041202-02-1
• 化学式: C₂₅H₂₉NO₅
• 分子量: 423.509
• InChiKey: HPVSEYQSCVMHNV-MPYDJNMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyl-3-[(E,2R,3R,4R,5S)-3,5-dihydroxy-2,4-dimethyl-7-phenylhept-6-enoyl]-1,3-oxazolidin-2-one 在 锂硼氢 作用下， 以 甲醇 为溶剂， 以66%的产率得到(2S,3S,4R,5S,E)-2,4-dimethyl-7-phenylhept-6-ene-1,3,5-triol
  参考文献：
  名称：

  Total synthesis of (+)-crocacin C

  摘要：

  Two approaches toward the total synthesis of cytotoxic polyketide natural product (+)-crocacin C (1) are described. The first approach, which was ultimately unsuccessful, was replaced altogether with a second that afforded target 1 in 10 linear steps from commercially available Evans' chiral propionimide (5% overall yield). No protecting groups were utilized in the total synthesis of 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.003
• 作为产物：
  描述：

  (E,2R,4R,5S)-1-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-5-hydroxy-2,4-dimethyl-7-phenylhept-6-ene-1,3-dione 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以88%的产率得到(4R)-4-benzyl-3-[(E,2R,3R,4R,5S)-3,5-dihydroxy-2,4-dimethyl-7-phenylhept-6-enoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Total synthesis of (+)-crocacin C

  摘要：

  Two approaches toward the total synthesis of cytotoxic polyketide natural product (+)-crocacin C (1) are described. The first approach, which was ultimately unsuccessful, was replaced altogether with a second that afforded target 1 in 10 linear steps from commercially available Evans' chiral propionimide (5% overall yield). No protecting groups were utilized in the total synthesis of 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.003

文献信息

• Concise Total Synthesis of (+)-Crocacin C
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1021/jo800906p

  日期：2008.8.1

  [GRAPHICS]The cytotoxic natural product (+)-crocacin C (1) has been synthesized in 10 linear steps from commercially available Evans' chiral propionimide. in 5% overall yield (8 steps from Evans' chiral dipropionate synthon). No protecting groups were utilized.
• Total synthesis of (+)-crocacin C
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1016/j.bmc.2010.03.003

  日期：2010.6.1

  Two approaches toward the total synthesis of cytotoxic polyketide natural product (+)-crocacin C (1) are described. The first approach, which was ultimately unsuccessful, was replaced altogether with a second that afforded target 1 in 10 linear steps from commercially available Evans' chiral propionimide (5% overall yield). No protecting groups were utilized in the total synthesis of 1. (C) 2010 Elsevier Ltd. All rights reserved.