(2R)-2-[[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]methyl]-2,3-dihydropyran-6-one | 1046769-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R)-2-[[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]methyl]-2,3-dihydropyran-6-one
• CAS: 1046769-78-1
• 化学式: C₃₅H₅₆O₆
• 分子量: 572.826
• InChiKey: ZIJGAKYNZRFKMO-RLFREQJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  41
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 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)-2-[[(2S,4S,6S)-6-[(3S)-3-(methoxymethoxy)heptadecyl]-2-phenyl-1,3-dioxan-4-yl]methyl]-2,3-dihydropyran-6-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以89%的产率得到(+)-passifloricin A
  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,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

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.