((S,4E)-5-((4R,5S)-5-((E)-4-(2-bromo-3,5-bis(methoxymethoxy)phenyl)but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-2-yloxy)(tert-butyl)dimethylsilane | 902128-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ((S,4E)-5-((4R,5S)-5-((E)-4-(2-bromo-3,5-bis(methoxymethoxy)phenyl)but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-2-yloxy)(tert-butyl)dimethylsilane
• 英文别名: [(E,2S)-5-[(4R,5S)-5-[(E)-4-[2-bromo-3,5-bis(methoxymethoxy)phenyl]but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]pent-4-en-2-yl]oxy-tert-butyl-dimethylsilane
• CAS: 902128-57-8
• 化学式: C₃₀H₄₉BrO₇Si
• 分子量: 629.704
• InChiKey: NGIMWUWGPVMSQG-PZOAXCLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.08
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((S,4E)-5-((4R,5S)-5-((E)-4-(2-bromo-3,5-bis(methoxymethoxy)phenyl)but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-2-yloxy)(tert-butyl)dimethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以95%的产率得到(E)-(S)-5-{(4R,5S)-5-[(E)-4-(2-Bromo-3,5-bis-methoxymethoxy-phenyl)-but-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pent-4-en-2-ol
  参考文献：
  名称：

  Enantioselective total synthesis of aigialomycin D

  摘要：

  An efficient, convergent approach for the total synthesis of aigialomycin D I is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hydroxy-bearing stereogenic centers at the C5' and C6' positions; (b) a Kocienski modified Julia protocol to construct the two E-configured double bonds; and (c) Yamaguchi macrolactonization to acccess the 14-membered macrocyclic ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.027
• 作为产物：
  描述：

  5-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-butane-1-sulfonyl]-1-phenyl-1H-tetrazole 、 2-甲氧基丙烯 、 (2E)-6-(benzyloxy)hex-2-en-1-ol 、 2-bromo-3,5-bis(methoxymethoxy)benzaldehyde 生成 ((S,4Z)-5-((4S,5R)-5-((E)-4-(2-bromo-3,5-bis(methoxymethoxy)phenyl)but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-2-yloxy)(tert-butyl)dimethylsilane 、 ((S,4E)-5-((4S,5R)-5-((E)-4-(2-bromo-3,5-bis(methoxymethoxy)phenyl)but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-2-yloxy)(tert-butyl)dimethylsilane 、 ((S,4Z)-5-((4R,5S)-5-((E)-4-(2-bromo-3,5-bis(methoxymethoxy)phenyl)but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-2-yloxy)(tert-butyl)dimethylsilane 、 ((S,4E)-5-((4R,5S)-5-((E)-4-(2-bromo-3,5-bis(methoxymethoxy)phenyl)but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-2-yloxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Enantioselective total synthesis of aigialomycin D

  摘要：

  An efficient, convergent approach for the total synthesis of aigialomycin D I is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hydroxy-bearing stereogenic centers at the C5' and C6' positions; (b) a Kocienski modified Julia protocol to construct the two E-configured double bonds; and (c) Yamaguchi macrolactonization to acccess the 14-membered macrocyclic ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.027

文献信息

• Enantioselective total synthesis of aigialomycin D
  作者：Jiangping Lu、Junying Ma、Xingang Xie、Bo Chen、Xuegong She、Xinfu Pan

  DOI：10.1016/j.tetasy.2006.03.027

  日期：2006.4

  An efficient, convergent approach for the total synthesis of aigialomycin D I is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hydroxy-bearing stereogenic centers at the C5' and C6' positions; (b) a Kocienski modified Julia protocol to construct the two E-configured double bonds; and (c) Yamaguchi macrolactonization to acccess the 14-membered macrocyclic ring. (c) 2006 Elsevier Ltd. All rights reserved.