(-)-(3R,5R,7R,9S,11S,13S,15S)-16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecan-1-ol | 948859-75-4

• 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: (-)-(3R,5R,7R,9S,11S,13S,15S)-16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecan-1-ol
• 英文别名: (3R,5R,7R,9S,11S,13S,15S)-16-[tert-butyl(diphenyl)silyl]oxy-3,5,7,9,11,13,15-heptamethylhexadecan-1-ol
• CAS: 948859-75-4
• 化学式: C₃₉H₆₆O₂Si
• 分子量: 595.037
• InChiKey: VVNWALJARATCOV-QJCLFNHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.74
• 重原子数：
  42
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(3R,5R,7R,9S,11S,13S,15S)-16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecan-1-ol 在 吡啶 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 (-)-(2S,4S,6S,8S,10S,12S,14S)-tert-butyl-(2,4,6,8,10,12,14-heptamethyl-triacontyloxy)-diphenyl-silane
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Phthioceranic Acid, a Heptamethyl-Branched Acid from Mycobacterium tuberculosis

  摘要：

  The first total synthesis of phthioceranic acid (1) has been achieved by an iterative catalytic asymmetric 1,4-addition protocol. This method provides a robust and high-yielding route for the preparation of 1,3-oligomethyl (deoxypropionate) arrays. After the desired number of methyl groups has been introduced, these arrays can be further functionalized at both ends to polymethyl-substituted lipids such as phthioceranic acid, a heptamethyl-branched fatty acid from the virulence factor Sulfolipid-I (2), found in Mycobacterium tuberculosis.

  DOI：

  10.1021/ol071078o
• 作为产物：
  描述：

  (tert-butyldiphenylsilanyloxy)acetaldehyde 在 palladium on activated charcoal 三乙基硅烷 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 288.19h， 生成 (-)-(3R,5R,7R,9S,11S,13S,15S)-16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecan-1-ol
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Phthioceranic Acid, a Heptamethyl-Branched Acid from Mycobacterium tuberculosis

  摘要：

  The first total synthesis of phthioceranic acid (1) has been achieved by an iterative catalytic asymmetric 1,4-addition protocol. This method provides a robust and high-yielding route for the preparation of 1,3-oligomethyl (deoxypropionate) arrays. After the desired number of methyl groups has been introduced, these arrays can be further functionalized at both ends to polymethyl-substituted lipids such as phthioceranic acid, a heptamethyl-branched fatty acid from the virulence factor Sulfolipid-I (2), found in Mycobacterium tuberculosis.

  DOI：

  10.1021/ol071078o

文献信息

• Catalytic Asymmetric Synthesis of Phthioceranic Acid, a Heptamethyl-Branched Acid from <i>Mycobacterium tuberculosis</i>
  作者：Bjorn ter Horst、Ben L. Feringa、Adriaan J. Minnaard

  DOI：10.1021/ol071078o

  日期：2007.8.1

  The first total synthesis of phthioceranic acid (1) has been achieved by an iterative catalytic asymmetric 1,4-addition protocol. This method provides a robust and high-yielding route for the preparation of 1,3-oligomethyl (deoxypropionate) arrays. After the desired number of methyl groups has been introduced, these arrays can be further functionalized at both ends to polymethyl-substituted lipids such as phthioceranic acid, a heptamethyl-branched fatty acid from the virulence factor Sulfolipid-I (2), found in Mycobacterium tuberculosis.