(2R,2'R,5R,5'R)-5,5'-bis-[(1R)-1-(hydroxy)undecyl]octahydro-2,2'-bifuran | 204441-26-9

• 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: (2R,2'R,5R,5'R)-5,5'-bis-[(1R)-1-(hydroxy)undecyl]octahydro-2,2'-bifuran
• 英文别名: dleta-lac-Acetogenin；(1R)-1-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]undecan-1-ol
• CAS: 204441-26-9
• 化学式: C₃₀H₅₈O₄
• 分子量: 482.788
• InChiKey: AUCMVFPGZUARCL-VHNXJUCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  34
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,2'R,5R,5'R)-5,5'-bis-[(1R)-1-(hydroxy)undecyl]octahydro-2,2'-bifuran 在 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,5R,2'R,5'R)-5,5'-Bis-((S)-1-azido-undecyl)-octahydro-[2,2']bifuranyl
  参考文献：
  名称：

  NOVEL CLASS OF DNA BINDING MOTIFS BASED ON BISTETRAHYDROFURAN AND BISFURAN SKELETON WITH LONG ALKYL CHAINS

  摘要：

  Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this paper, new DNA binding molecules; diamino-bistetrahydrofuran (bisTHF) and diamino-bisfuran are reported. The bisTHF ligand with RR configuration at the amino groups and C8 alkyl chains (RR8) stabilized GC-rich duplex. In contrast, bisfuran compounds stabilized AT-rich duplex. The binding affinity of RR8 with 12 mer duplex DNA was determined by isothermal titration calorimetry to be 3.3 x 10(8) M-1.

  DOI：

  10.1081/ncn-100002331
• 作为产物：
  描述：

  (-)-(2S,3R,6R,7R,10R,11S)-1,12-O-Bis(4-nitrobenzoyl)-3,6:7,10-diepoxy-1,2,11,12-tetrahydroxydodecane 在 四丁基氢氧化铵 、 三乙胺 、 copper(I) bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 5.5h， 生成 (2R,2'R,5R,5'R)-5,5'-bis-[(1R)-1-(hydroxy)undecyl]octahydro-2,2'-bifuran
  参考文献：
  名称：

  Novel acyclic ligands for metal cations based on the adjacent bistetrahydrofuran as analogs of natural Annonaceous acetogenins

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(97)10439-2

文献信息

• [3 + 2]-Annulation Reactions of Chiral Allylsilanes and Chiral Aldehydes. Studies on the Synthesis of Bis-tetrahydrofuran Substructures of Annonaceous Acetogenins
  作者：Eric Mertz、Jennifer M. Tinsley、William R. Roush

  DOI：10.1021/jo0511290

  日期：2005.9.1

  Double asymmetric [3 + 2]-annulation reactions of chiral β-silyloxyallylsilanes with chiral 2-tetrahydrofuranyl carboxaldehydes have been studied, leading to the stereocontrolled synthesis of six diastereomeric bis-tetrahydrofuran structures corresponding to the core subunits of members of the Annonaceous acetogenin family of natural products. Transition-state models are proposed to account for the

  研究了手性β-甲硅烷氧基烯丙基硅烷与手性2-四氢呋喃基甲醛的双不对称[3 + 2]环化反应，导致立体控制合成了六个非对映体双-四氢呋喃结构，这些结构对应于环己酮产乙酸甘油酯家族成员的核心亚基。天然产物。提出过渡态模型以说明双立体分化[3 + 2]环化反应的立体选择性。
• Efficient Protiodesilylation of Unactivated C(sp³)−SiMe₂Ph Bonds Using Tetrabutylammonium Fluoride
  作者：Cheryl L. Heitzman、William T. Lambert、Eric Mertz、J. Brad Shotwell、Jennifer M. Tinsley、Porino Va、William R. Roush

  DOI：10.1021/ol0506821

  日期：2005.6.1

  [reaction: see text] The protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds proceeds efficiently by treatment with tetrabutylammonium fluoride in wet DMF or THF via isolable dimethylsilanol intermediates.

  [反应：见正文] 通过可分离的二甲基硅烷醇中间体，用四丁基氟化铵在湿 DMF 或 THF 中进行处理，可以有效地进行未活化的 C(sp3)-SiMe2Ph 键的脱甲硅烷基化。
• NOVEL CLASS OF DNA BINDING MOTIFS BASED ON BISTETRAHYDROFURAN AND BISFURAN SKELETON WITH LONG ALKYL CHAINS
  作者：Shigeki Sasaki、Takayuki Shibata、Hidemine Torigoe、Yosinori Shibata、Minoru Maeda

  DOI：10.1081/ncn-100002331

  日期：2001.3.31

  Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this paper, new DNA binding molecules; diamino-bistetrahydrofuran (bisTHF) and diamino-bisfuran are reported. The bisTHF ligand with RR configuration at the amino groups and C8 alkyl chains (RR8) stabilized GC-rich duplex. In contrast, bisfuran compounds stabilized AT-rich duplex. The binding affinity of RR8 with 12 mer duplex DNA was determined by isothermal titration calorimetry to be 3.3 x 10(8) M-1.
• 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.