(2E)-ethyl 3-((3R,9S,4E)-(9-tert-butyldimethylsilyloxy)-1-(1,3-dithian-2-yl)dec-4-en-3-yloxy)acrylate | 1292793-78-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E)-ethyl 3-((3R,9S,4E)-(9-tert-butyldimethylsilyloxy)-1-(1,3-dithian-2-yl)dec-4-en-3-yloxy)acrylate
• CAS: 1292793-78-2
• 化学式: C₂₅H₄₆O₄S₂Si
• 分子量: 502.855
• InChiKey: LXXNWSFJCIYKKM-BUPSZGMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  32.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2E)-ethyl 3-((3R,9S,4E)-(9-tert-butyldimethylsilyloxy)-1-(1,3-dithian-2-yl)dec-4-en-3-yloxy)acrylate 在 碳酸氢钠 、 碘甲烷 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以96%的产率得到(2E)-ethyl 3-((4R,10S,E)-10-(tert-butyldimethylsilyloxy)-1-oxoundec-5-en-4-yloxy)prop-2-enoate
  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：

  (9S,4E)-(9-tert-butyldimethylsilyloxy)-1-(1,3-dithian-2-yl)dec-4-en-3-ol 、 丙炔酸乙酯 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 以94%的产率得到(2E)-ethyl 3-((3R,9S,4E)-(9-tert-butyldimethylsilyloxy)-1-(1,3-dithian-2-yl)dec-4-en-3-yloxy)acrylate
  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