(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol | 1551543-36-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol
• 英文别名: (3S,4S,5E,7R,8S,9R,10R)-8-[tert-butyl(dimethyl)silyl]oxy-10-methoxy-12-[(4-methoxyphenyl)methoxy]-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol
• CAS: 1551543-36-2
• 化学式: C₃₁H₅₄O₅Si
• 分子量: 534.852
• InChiKey: JTTRTKNSWVRVIM-DYSLNYBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.41
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 5%-palladium/activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 (3aR,6S,7S,8E,11R,13aR,E)-6-((4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-9-hydroxy-7-methoxy-4,6-dimethylnon-2-en-2-yl)-2,2,7,11-tetramethyl-6,7,8,9,10,11-hexahydro-3aH-[1,3]dioxolo[4,5-c ][1]oxacyclododecin-4(13aH)-one
  参考文献：
  名称：

  A Concise Synthesis of Carolacton

  摘要：

  A synthesis of carolacton, a myxobacterial natural product that has profound effects on Streptococcus mutans biofilms, is reported. The synthesis proceeds via a longest linear sequence of 14 steps from an Evans beta-ketoimide and enabled preliminary evaluations of the effects of late-stage intermediates on S. mutans biofilms. These studies suggest that further investigations into carolacton's structure function relationships are warranted.

  DOI：

  10.1021/ol500004k
• 作为产物：
  描述：

  (2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 锂硼氢 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 (R,R)-trans-EZ-crotyl mix 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 69.33h， 生成 (3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol
  参考文献：
  名称：

  A Concise Synthesis of Carolacton

  摘要：

  A synthesis of carolacton, a myxobacterial natural product that has profound effects on Streptococcus mutans biofilms, is reported. The synthesis proceeds via a longest linear sequence of 14 steps from an Evans beta-ketoimide and enabled preliminary evaluations of the effects of late-stage intermediates on S. mutans biofilms. These studies suggest that further investigations into carolacton's structure function relationships are warranted.

  DOI：

  10.1021/ol500004k

文献信息

• A Concise Synthesis of Carolacton
  作者：Michal S. Hallside、Richard S. Brzozowski、William M. Wuest、Andrew J. Phillips

  DOI：10.1021/ol500004k

  日期：2014.2.21

  A synthesis of carolacton, a myxobacterial natural product that has profound effects on Streptococcus mutans biofilms, is reported. The synthesis proceeds via a longest linear sequence of 14 steps from an Evans beta-ketoimide and enabled preliminary evaluations of the effects of late-stage intermediates on S. mutans biofilms. These studies suggest that further investigations into carolacton's structure function relationships are warranted.