[(1S,4R,5S)-4,5-bis(phenylmethoxy)-1,3-bis(phenylmethoxymethyl)cyclopent-2-en-1-yl]oxymethylbenzene | 250721-97-2

• 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: [(1S,4R,5S)-4,5-bis(phenylmethoxy)-1,3-bis(phenylmethoxymethyl)cyclopent-2-en-1-yl]oxymethylbenzene
• CAS: 250721-97-2
• 化学式: C₄₂H₄₂O₅
• 分子量: 626.792
• InChiKey: PNMYGJTXFGWANT-IWSHAHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1S,4R,5S)-4,5-bis(phenylmethoxy)-1,3-bis(phenylmethoxymethyl)cyclopent-2-en-1-yl]oxymethylbenzene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以99%的产率得到(1R,2R,3S,4S)-2,3,4-trihydroxy-4(hydroxymethyl)cyclopentanylmethanol
  参考文献：
  名称：

  Total Synthesis of Carba-d-fructofuranose via a Novel Metathesis Reaction

  摘要：

  [GRAPHICS]Carba-o-fructofuranose 2b was synthesized in 11 steps (45%), from 2,3,5-tri-O-benzyl-D-arabinofuranose 5 using a ring closing metathesis. Schrock's catalyst was employed on the unique substituted diene synthon 4 to furnish the pentahydroxlated cyclopentene 3. Hydrogenation afforded 2b.

  DOI：

  10.1021/ol990275n
• 作为产物：
  描述：

  [(3S,4S,5R)-4,5-bis(phenylmethoxy)-3,6-bis(phenylmethoxymethyl)hepta-1,6-dien-3-yl]oxymethylbenzene 在 bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum 作用下， 以 正己烷 为溶剂， 反应 18.0h， 以91%的产率得到[(1S,4R,5S)-4,5-bis(phenylmethoxy)-1,3-bis(phenylmethoxymethyl)cyclopent-2-en-1-yl]oxymethylbenzene
  参考文献：
  名称：

  Total Synthesis of Carba-d-fructofuranose via a Novel Metathesis Reaction

  摘要：

  [GRAPHICS]Carba-o-fructofuranose 2b was synthesized in 11 steps (45%), from 2,3,5-tri-O-benzyl-D-arabinofuranose 5 using a ring closing metathesis. Schrock's catalyst was employed on the unique substituted diene synthon 4 to furnish the pentahydroxlated cyclopentene 3. Hydrogenation afforded 2b.

  DOI：

  10.1021/ol990275n

文献信息

• Total Synthesis of Carba-<scp>d</scp>-fructofuranose via a Novel Metathesis Reaction
  作者：Mohindra Seepersaud、Yousef Al-Abed

  DOI：10.1021/ol990275n

  日期：1999.11.1

  [GRAPHICS]Carba-o-fructofuranose 2b was synthesized in 11 steps (45%), from 2,3,5-tri-O-benzyl-D-arabinofuranose 5 using a ring closing metathesis. Schrock's catalyst was employed on the unique substituted diene synthon 4 to furnish the pentahydroxlated cyclopentene 3. Hydrogenation afforded 2b.