[(2R)-1-[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-yl] prop-2-enoate | 1046769-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: [(2R)-1-[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-yl] prop-2-enoate
• CAS: 1046769-77-0
• 化学式: C₃₇H₆₀O₆
• 分子量: 600.88
• InChiKey: OHSCEBRJWFMFPH-JSKKBBOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  43
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R)-1-[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-yl] prop-2-enoate 在 Grubbs' catalyst (1st generation) 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以92%的产率得到(2R)-2-[[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]methyl]-2,3-dihydropyran-6-one
  参考文献：
  名称：

  Asymmetric synthesis of (+)-passifloricin A and its 6-epimer

  摘要：

  Stereoselective total syntheses of the antiprotozoal natural product (+)-passifloricin A and its C-6 epimer have been achieved in similar to 5% overall yield. The strategy is based on Jacobsen epoxidation, Grubbs' metathesis and an Evans' intramolecular oxa-Michael reaction. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.070
• 作为产物：
  描述：

  (2R)-1-[(2S,4R,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol 、 丙烯酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到[(2R)-1-[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-yl] prop-2-enoate
  参考文献：
  名称：

  Asymmetric synthesis of (+)-passifloricin A and its 6-epimer

  摘要：

  Stereoselective total syntheses of the antiprotozoal natural product (+)-passifloricin A and its C-6 epimer have been achieved in similar to 5% overall yield. The strategy is based on Jacobsen epoxidation, Grubbs' metathesis and an Evans' intramolecular oxa-Michael reaction. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.070

文献信息

• Asymmetric synthesis of (+)-passifloricin A and its 6-epimer
  作者：S. Chandrasekhar、Ch. Rambabu、A. Syamprasad Reddy

  DOI：10.1016/j.tetlet.2008.05.070

  日期：2008.7

  Stereoselective total syntheses of the antiprotozoal natural product (+)-passifloricin A and its C-6 epimer have been achieved in similar to 5% overall yield. The strategy is based on Jacobsen epoxidation, Grubbs' metathesis and an Evans' intramolecular oxa-Michael reaction. (c) 2008 Elsevier Ltd. All rights reserved.