(Z)-(1R,4R,5R)-1-[(2R,5R)-5-((R)-1,4-Dihydroxy-butyl)-tetrahydro-furan-2-yl]-1-iodo-pentadec-8-ene-4,5-diol | 444884-27-9

• 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: (Z)-(1R,4R,5R)-1-[(2R,5R)-5-((R)-1,4-Dihydroxy-butyl)-tetrahydro-furan-2-yl]-1-iodo-pentadec-8-ene-4,5-diol
• CAS: 444884-27-9
• 化学式: C₂₃H₄₃IO₅
• 分子量: 526.496
• InChiKey: ITOVFOIPYMBFRS-GWNUESPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  29.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  90.15
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-(1R,4R,5R)-1-[(2R,5R)-5-((R)-1,4-Dihydroxy-butyl)-tetrahydro-furan-2-yl]-1-iodo-pentadec-8-ene-4,5-diol 在 二正丁基氧化锡 作用下， 以 苯 为溶剂， 反应 17.0h， 以71%的产率得到(R)-1-[(2R,5R,2'S,5'R)-5'-((Z)-(R)-1-Hydroxy-undec-4-enyl)-octahydro-[2,2']bifuranyl-5-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
• 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 硫酸 、 sodium hexamethyldisilazane 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 15.0h， 生成 (Z)-(1R,4R,5R)-1-[(2R,5R)-5-((R)-1,4-Dihydroxy-butyl)-tetrahydro-furan-2-yl]-1-iodo-pentadec-8-ene-4,5-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

文献信息

• A novel desymmetrization reaction of an acetogenin precursor: A formal synthesis of trilobacin and asimicin
  作者：Zheming Ruan、David R. Mootoo

  DOI：10.1016/s0040-4039(98)80016-6

  日期：1999.1

  A two-directional strategy which is based on the haloetherification reaction of a bis-5,6-O-isopropylidene alkene, is applied to the synthesis of a versatile relay compound for the bis-THF containing acetogenins. (C) 1998 Elsevier Science Ltd. All rights reserved.