(-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane | 165960-92-9

• 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: (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane
• 英文别名: [(2S)-2-hydroxy-2-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-methylsulfonyloxy-2-(4-nitrobenzoyl)oxyethyl]oxolan-2-yl]oxolan-2-yl]ethyl] 4-nitrobenzoate
• CAS: 165960-92-9
• 化学式: C₂₇H₃₀N₂O₁₄S
• 分子量: 638.606
• InChiKey: MMXAMPJRWPFLDC-AFRKUKOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  235
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane 在 吡啶 、 chromium(VI) oxide 、 sodium amalgam 、 正丁基锂 、 二甲基硫 、 硫酸 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 四丁基氟化铵 、 四丁基氢氧化铵 、 氨 、 potassium carbonate 、 N,N-二异丙基乙胺 、 copper(I) bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 106.17h， 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：

  (-)-(2S,3S,6R,7R,10S,11S)-2,3:10,11-Diepoxy-6,7-O-isopropylidene-1,12-O-bis(4-nitrobenzoyl)-1,6,7,12-tetrahydroxydodecane 在 三氟化硼乙醚 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-2-O-methanesulfonyl-1,2,11,12-tetrahydroxydodecane
  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

• Novel acyclic ligands for metal cations based on the adjacent bistetrahydrofuran as analogs of natural Annonaceous acetogenins
  作者：Shigeki Sasaki、Katsunori Maruta、Hiroyuki Naito、Rie Maemura、Eiji Kawahara、Minoru Maeda

  DOI：10.1016/s0040-4020(97)10439-2

  日期：1998.3

  The acyclic ligands with an adjacent bistetrahydrofuran (THF) skeleton have been synthesized as analogs of bullatacin, a representative natural product in a family of Annonaceous acetogenins, and their binding properties toward metal cations have been investigated. The dihydroxyl bis-THF ligands with alkyl chains showed specific binding toward Ca2+, and those with acetamido groups exhibited potent binding with Ca2+ and Mg2+. The ligand with ether chains showed higher affinity toward Mg2+. These binding properties which depend on the nature of side chains and their stereochemistry have been analyzed by molecular modeling. (C) 1998 Elsevier Science Ltd. All rights reserved.