(-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester | 948859-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester
• 英文别名: [(3R,5R,7R,9S,11S,13S,15S)-16-[tert-butyl(diphenyl)silyl]oxy-3,5,7,9,11,13,15-heptamethylhexadecyl] 4-methylbenzenesulfonate
• CAS: 948859-76-5
• 化学式: C₄₆H₇₂O₄SSi
• 分子量: 749.227
• InChiKey: VNSVEUADEJFBGG-FVMQRRFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.46
• 重原子数：
  52
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester 在 四丁基氟化铵 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 (-)-(2S,4S,6S,8S,10S,12S,14S)-2,4,6,8,10,12,14-heptamethyl-triacontan-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
• 作为产物：
  描述：

  (-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester 在 palladium on activated charcoal 吡啶 、 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 271.02h， 生成 (-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester
  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