(R)-1-{(2R,5R)-5-[(R)-3-((4R,5R)-5-But-3-enyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-iodo-propyl]-tetrahydro-furan-2-yl}-butane-1,4-diol | 444884-30-4

• 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: (R)-1-{(2R,5R)-5-[(R)-3-((4R,5R)-5-But-3-enyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-iodo-propyl]-tetrahydro-furan-2-yl}-butane-1,4-diol
• CAS: 444884-30-4
• 化学式: C₂₀H₃₅IO₅
• 分子量: 482.399
• InChiKey: BBDHQPIWGYHYAW-MGYGNFHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-1-{(2R,5R)-5-[(R)-3-((4R,5R)-5-But-3-enyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-iodo-propyl]-tetrahydro-furan-2-yl}-butane-1,4-diol 在 三氟化硼乙醚 、 二正丁基氧化锡 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 67.0h， 生成 (R)-(2S,5R,2'R,5'R,2''R)-1-(Dodecahydro-[2,2';5',2'']terfuran-5-yl)-pent-4-en-1-ol
  参考文献：
  名称：

  1,2-O-Isopropylidene-5-alkene templates for the synthesis of oligo-tetrahydrofurans

  摘要：

  The highly functionalized THF 4 was prepared in eight steps from 2,5-cyclooctadiene. The key step in this synthesis was a novel desymmetrization reaction involving the iodoetherification of the C2 symmetric bis-isopropylidene alkene 6 to THF 4. The versatility of 4 was demonstrated by its conversion to bis-THF 3, a known precursor for trilobacin, and to the tris-THF-lactone 5, a potential relay compound for cyclic polyether analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00075-3
• 作为产物：
  描述：

  3-((4R,5R)-5-{(R)-3-[(2R,5R)-5-((R)-2,2-Dimethyl-[1,3]dioxepan-4-yl)-tetrahydro-furan-2-yl]-3-iodo-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde 在 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 4.0h， 生成 (R)-1-{(2R,5R)-5-[(R)-3-((4R,5R)-5-But-3-enyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-iodo-propyl]-tetrahydro-furan-2-yl}-butane-1,4-diol
  参考文献：
  名称：

  1,2-O-Isopropylidene-5-alkene templates for the synthesis of oligo-tetrahydrofurans

  摘要：

  The highly functionalized THF 4 was prepared in eight steps from 2,5-cyclooctadiene. The key step in this synthesis was a novel desymmetrization reaction involving the iodoetherification of the C2 symmetric bis-isopropylidene alkene 6 to THF 4. The versatility of 4 was demonstrated by its conversion to bis-THF 3, a known precursor for trilobacin, and to the tris-THF-lactone 5, a potential relay compound for cyclic polyether analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00075-3