methyl (E,5S,6R)-5-methyl-6-[(2-methylpropan-2-yl)oxycarbonylamino]-7-phenylmethoxyhept-3-enoate | 181633-57-8

• 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: methyl (E,5S,6R)-5-methyl-6-[(2-methylpropan-2-yl)oxycarbonylamino]-7-phenylmethoxyhept-3-enoate
• CAS: 181633-57-8
• 化学式: C₂₁H₃₁NO₅
• 分子量: 377.481
• InChiKey: CFCDUQPLVWIBGC-JIMORPAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E,5S,6R)-5-methyl-6-[(2-methylpropan-2-yl)oxycarbonylamino]-7-phenylmethoxyhept-3-enoate 在 sodium tetrahydroborate 、 二甲基硫 、 臭氧 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,2R)-1-Benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propylamine
  参考文献：
  名称：

  直接合成乌拉泊肽的研究。C8-C25 Tris-Oxazole片段的不对称合成。

  摘要：

  DOI：

  10.1021/jo960532r
• 作为产物：
  描述：

  氨基甲酸叔丁酯 、 苄氧基乙醛 、 4-己烯酸,3-(二甲基苯基甲硅烷基)-,甲基酯,(3S,4E)- 在 三氟化硼乙醚 作用下， 以73%的产率得到methyl (E,5S,6R)-5-methyl-6-[(2-methylpropan-2-yl)oxycarbonylamino]-7-phenylmethoxyhept-3-enoate
  参考文献：
  名称：

  Asymmetric synthesis of a C1C19 fragment of ulapualide A

  摘要：

  The stereocontrolled synthesis of a C1-C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsen's hydrolytic kinetic resolution (HKR) of a terminal epoxide. while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1-C6 and the C7-C19 fragments by a Kishi-Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01553-8

文献信息

• Studies Directed toward the Synthesis of Ulapualide A. Asymmetric Synthesis of the C8−C25 Tris-Oxazole Fragment
  作者：James S. Panek、Richard T. Beresis

  DOI：10.1021/jo960532r

  日期：1996.1.1
• Asymmetric synthesis of a C1C19 fragment of ulapualide A
  作者：Cassandra A. Celatka、James S. Panek

  DOI：10.1016/s0040-4039(02)01553-8

  日期：2002.9

  The stereocontrolled synthesis of a C1-C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsen's hydrolytic kinetic resolution (HKR) of a terminal epoxide. while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1-C6 and the C7-C19 fragments by a Kishi-Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment. (C) 2002 Elsevier Science Ltd. All rights reserved.