Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester | 165961-06-8

• 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: Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester
• CAS: 165961-06-8
• 化学式: C₄₀H₇₂O₁₀SSi
• 分子量: 773.157
• InChiKey: ARJSKPYDYNNQEY-YQAKARPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  52.0
• 可旋转键数：
  26.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  129.98
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester 在 potassium carbonate 、 N,N-二异丙基乙胺 、 copper(I) bromide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 25.17h， 生成 (+)-(4R,15R,16R,19R,20R,23R,24S)-1-O-(tert-Butyldimethylsilyl)-16,19:20,23-diepoxy-1,4,15,24-tetrahydroxy-4,15,24-O-tris(methoxymethyl)tetratriacontane
  参考文献：
  名称：

  The First Total Synthesis of (+)-Bullatacin, a Potent Antitumor Annonaceous Acetogenin, and (+)-(15,24)-bis-epi-Bullatacin

  摘要：

  This paper reports the first total synthesis of the natural product (+)-bullatacin (1), a representative of potent antitumor Annonaceous acetogenins, as well as a stereoisomer (+)-(15,24)-bisepi-bullatacin (2). In this synthesis, a new, efficient method has been developed to introduce the gamma-lactone into the bistetrahydrofuran skeleton through in situ alkylation of epoxide 4 by the alpha-sulfonyl carbanion of phenyl sulfone 5. The methylated gamma-lactone was successfully synthesized by a sequence of reactions comprising an aldol reaction, an acidic lactonization, and elimination under mild, basic condition.

  DOI：

  10.1021/jo00119a019
• 作为产物：
  描述：

  [(4R)-13-(benzenesulfonyl)-4-(methoxymethoxy)tridecoxy]-tert-butyl-dimethylsilane 在 吡啶 、 sodium amalgam 、 正丁基锂 作用下， 以 乙二醇二甲醚 、 乙醇 、 正己烷 为溶剂， 反应 72.17h， 生成 Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-15-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-methoxymethoxy-pentadecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester
  参考文献：
  名称：

  The First Total Synthesis of (+)-Bullatacin, a Potent Antitumor Annonaceous Acetogenin, and (+)-(15,24)-bis-epi-Bullatacin

  摘要：

  This paper reports the first total synthesis of the natural product (+)-bullatacin (1), a representative of potent antitumor Annonaceous acetogenins, as well as a stereoisomer (+)-(15,24)-bisepi-bullatacin (2). In this synthesis, a new, efficient method has been developed to introduce the gamma-lactone into the bistetrahydrofuran skeleton through in situ alkylation of epoxide 4 by the alpha-sulfonyl carbanion of phenyl sulfone 5. The methylated gamma-lactone was successfully synthesized by a sequence of reactions comprising an aldol reaction, an acidic lactonization, and elimination under mild, basic condition.

  DOI：

  10.1021/jo00119a019