(+)-(4R,15R,16R,19R,20R,23R,24S)-16,19:20,23-Diepoxy-1,4,15,24-tetrahydroxy-4,15,24-O-tris(methoxymethyl)tetratriacontanoic acid methyl ester | 165961-11-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-(4R,15R,16R,19R,20R,23R,24S)-16,19:20,23-Diepoxy-1,4,15,24-tetrahydroxy-4,15,24-O-tris(methoxymethyl)tetratriacontanoic acid methyl ester
• 英文别名: methyl (4R,15R)-4,15-bis(methoxymethoxy)-15-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-(methoxymethoxy)undecyl]oxolan-2-yl]oxolan-2-yl]pentadecanoate
• CAS: 165961-11-5
• 化学式: C₄₁H₇₈O₁₀
• 分子量: 731.064
• InChiKey: SFYYKLMEQVZIRJ-QHACAUIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  51
• 可旋转键数：
  36
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (+)-(4R,15R,16R,19R,20R,23R,24S)-16,19:20,23-Diepoxy-1,4,15,24-tetrahydroxy-4,15,24-O-tris(methoxymethyl)tetratriacontanoic acid methyl ester 在 吡啶 、 二甲基硫 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 氨 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 5.5h， 生成 (5S)-3-[(2R,13R)-2,13-二羟基-13-{(2R,2'R,5'R)-5'-[(1S)-1-羟基十一烷基]八氢-2,2'-联呋喃-5-基}十三烷基]-5-甲基呋喃-2(5H)-酮
  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：

  nonylmagnesium bromide 在 chromium(VI) oxide 、 硫酸 、 四丁基氟化铵 、 N,N-二异丙基乙胺 、 copper(I) bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 27.33h， 生成 (+)-(4R,15R,16R,19R,20R,23R,24S)-16,19:20,23-Diepoxy-1,4,15,24-tetrahydroxy-4,15,24-O-tris(methoxymethyl)tetratriacontanoic acid methyl 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

文献信息

• The First Total Synthesis of (+)-Bullatacin, a Potent Antitumor Annonaceous Acetogenin, and (+)-(15,24)-bis-epi-Bullatacin
  作者：Hiroyuki Naito、Eiji Kawahara、Katsunori Maruta、Minoru Maeda、Shigeki Sasaki

  DOI：10.1021/jo00119a019

  日期：1995.7

  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.