2-[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]acetaldehyde | 1046769-76-9

• 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: 2-[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]acetaldehyde
• CAS: 1046769-76-9
• 化学式: C₃₁H₅₂O₅
• 分子量: 504.751
• InChiKey: OGIFDZBYLVYTFV-MBEDZMRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  36
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]acetaldehyde 、 3-溴丙烯 在 氯化铵 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2R)-1-[(2S,4R,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol 、 (2S)-1-[(2S,4R,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol
  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：

  ethyl 2-{(2S,4R,6R)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl}acetate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到2-[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]acetaldehyde
  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.