| 1292793-80-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 1292793-80-6
• 化学式: C₁₈H₃₂O₆
• 分子量: 344.448
• InChiKey: KIYIPPUILPHLSR-NLMSKWTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以95%的产率得到2-((2R,3S,6R)-6-((S,E)-6-hydroxyhept-1-en-1-yl)-3-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)acetic acid
  参考文献：
  名称：

  Formal total synthesis of aspergillide A

  摘要：

  The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C-4-C-14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into beta-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.016
• 作为产物：
  描述：

  ethyl 2-((2R,3S,6R)-6-((6S,1E)-6-(tert-butyldimethylsilyloxy)hept-1-enyl)-3-methoxymethyloxytetrahydro-2H-pyran-2-yl)acetate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以100%的产率得到
  参考文献：
  名称：

  Formal total synthesis of aspergillide A

  摘要：

  The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C-4-C-14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into beta-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.016