(E,4S,5R,6R)-4,5,6-tris[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-7-oxooct-2-enal | 1395502-33-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,4S,5R,6R)-4,5,6-tris[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-7-oxooct-2-enal
• CAS: 1395502-33-6
• 化学式: C₂₇H₅₆O₅Si₃
• 分子量: 544.995
• InChiKey: LDHAVYTWVRSRAB-LNFHCZDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.89
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E,4S,5R,6R)-4,5,6-tris[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-7-oxooct-2-enal 、 (2E,4E,6E)-8-(Diethoxy-phosphoryl)-4,6-dimethyl-octa-2,4,6-trienoic acid methyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.92h， 以56.522%的产率得到
  参考文献：
  名称：

  Synthesis and Structure of Two New Mycolactones Isolated from M. ulcerans subsp. shinshuense

  摘要：

  Two new mycolactones, mycolactones S1 and S2, were isolated from culture agar of Mycobacterium ulcerans subsp. shinshuense. Their structures were established in a three-step procedure: (1) probable structures were speculated from MS analysis; (2) candidates were synthesized; (3) HPLC profiles were established for identification of the natural products. Newly isolated mycolactones correspond to the "oxidized forms" of mycolactone NB, the causative toxin of Buruli ulcer, isolated from Mycobacterium ulcerans.

  DOI：

  10.1021/ol302072b
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 甲酸 、 三氧化硫吡啶 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 silver nitrate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.53h， 生成 (E,4S,5R,6R)-4,5,6-tris[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-7-oxooct-2-enal
  参考文献：
  名称：

  Synthesis and Structure of Two New Mycolactones Isolated from M. ulcerans subsp. shinshuense

  摘要：

  Two new mycolactones, mycolactones S1 and S2, were isolated from culture agar of Mycobacterium ulcerans subsp. shinshuense. Their structures were established in a three-step procedure: (1) probable structures were speculated from MS analysis; (2) candidates were synthesized; (3) HPLC profiles were established for identification of the natural products. Newly isolated mycolactones correspond to the "oxidized forms" of mycolactone NB, the causative toxin of Buruli ulcer, isolated from Mycobacterium ulcerans.

  DOI：

  10.1021/ol302072b

文献信息

• Synthesis and Structure of Two New Mycolactones Isolated from <i>M. ulcerans</i> subsp. <i>shinshuense</i>
  作者：Sudhir M. Hande、Yuko Kazumi、W. George Lai、Katrina L. Jackson、Shinji Maeda、Yoshito Kishi

  DOI：10.1021/ol302072b

  日期：2012.9.7

  Two new mycolactones, mycolactones S1 and S2, were isolated from culture agar of Mycobacterium ulcerans subsp. shinshuense. Their structures were established in a three-step procedure: (1) probable structures were speculated from MS analysis; (2) candidates were synthesized; (3) HPLC profiles were established for identification of the natural products. Newly isolated mycolactones correspond to the "oxidized forms" of mycolactone NB, the causative toxin of Buruli ulcer, isolated from Mycobacterium ulcerans.