(5R,5'R)-5,5'-[(1R,2R)-1,2-dibenzyloxyethane-1,2-diyl]bis[2(5H)-furanone] | 222736-63-2

• 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: (5R,5'R)-5,5'-[(1R,2R)-1,2-dibenzyloxyethane-1,2-diyl]bis[2(5H)-furanone]
• 英文别名: (2R)-2-[(1R,2R)-2-[(2R)-5-oxo-2H-furan-2-yl]-1,2-bis(phenylmethoxy)ethyl]-2H-furan-5-one
• CAS: 222736-63-2
• 化学式: C₂₄H₂₂O₆
• 分子量: 406.435
• InChiKey: PLISHQMQWJVADP-FAYOUJPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5R,5'R)-5,5'-[(1R,2R)-1,2-dibenzyloxyethane-1,2-diyl]bis[2(5H)-furanone] 以 丙酮 为溶剂， 反应 4.0h， 以76%的产率得到(1S,1'S,2R,2'R,4S,4'S,5R,5'R)-4,4'-bis[2-phenyl-3,6-dioxabicyclo[3.2.1]octan-7-one]
  参考文献：
  名称：

  C2-对称的对映体纯净的双（α，β-丁烯内酯）对映体作为不对称合成的模板。在合成（+）-大戟醇中的应用。

  摘要：

  从D-甘露醇开始，我们准备了几个C（2）对称的乙醚双（α，β-丁烯内酯）对称并研究了它们与乙烯的[2 + 2]光环加成反应。中央二醇单元的保护基对环加成的面部选择性具有显着影响，双（三甲基甲硅烷基氧基）衍生物表现出最高的非对映选择性。基态底物的理论构象分析与实验观察到的非对面选择性非常吻合。该双（光环加合物）已被转化为对映纯环丁烷，该对映体是由乙烯与γ-羟甲基-α，β-丁烯内酯的光反应正式形成的，其中先前仅发现了中等的面部选择性。作为这些研究的应用，

  DOI：

  10.1021/jo026705w
• 作为产物：
  描述：

  phenylselenoacetic acid dianion 、 1,2:5,6-Dianhydro-3,4-di-O-benzyl-D-mannitol 在 双氧水 、 溶剂黄146 作用下， 生成 (5R,5'R)-5,5'-[(1R,2R)-1,2-dibenzyloxyethane-1,2-diyl]bis[2(5H)-furanone]
  参考文献：
  名称：

  C2-symmetric enantiopure bis-α,β-butenolides as diastereoselective substrates in ethylene photocycloaddition

  摘要：

  Several C-2-symmetric bis-alpha,beta-butenolides have been synthesised starting from D-mannitol. Their [2+2]-photocycloaddition to ethylene has been studied as a model reaction to evaluate the influence of the protecting groups of the central diol system on the facial diastereoselectivity. The trimethylsilyl derivative shows the highest selectivity. The bis-cyclobutane containing products have been converted into the enantiopure adducts of gamma-hydroxymethyl-alpha,beta-butenolide and ethylene. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00172-0

文献信息

• <i>C</i>₂-Symmetric Enantiopure Ethanotethered Bis(α,β-butenolides) as Templates for Asymmetric Synthesis. Application to the Synthesis of (+)-Grandisol¹
  作者：Pedro de March、Marta Figueredo、Josep Font、Javier Raya、Angel Alvarez-Larena、Juan F. Piniella

  DOI：10.1021/jo026705w

  日期：2003.3.1

  Starting from D-mannitol, we have prepared several C(2)-symmetric ethanotethered bis(alpha,beta-butenolides) and studied their [2+2] photocycloaddition reaction with ethylene. The protective groups of the central diol unit have a noticeable influence on the facial selectivity of the cycloaddition, the bis(trimethylsilyloxy) derivatives showing the highest diastereoselectivity. A theoretical conformational

  从D-甘露醇开始，我们准备了几个C（2）对称的乙醚双（α，β-丁烯内酯）对称并研究了它们与乙烯的[2 + 2]光环加成反应。中央二醇单元的保护基对环加成的面部选择性具有显着影响，双（三甲基甲硅烷基氧基）衍生物表现出最高的非对映选择性。基态底物的理论构象分析与实验观察到的非对面选择性非常吻合。该双（光环加合物）已被转化为对映纯环丁烷，该对映体是由乙烯与γ-羟甲基-α，β-丁烯内酯的光反应正式形成的，其中先前仅发现了中等的面部选择性。作为这些研究的应用，
• C2-symmetric enantiopure bis-α,β-butenolides as diastereoselective substrates in ethylene photocycloaddition
  作者：Pedro de March、Marta Figueredo、Josep Font、Javier Raya

  DOI：10.1016/s0040-4039(99)00172-0

  日期：1999.3

  Several C-2-symmetric bis-alpha,beta-butenolides have been synthesised starting from D-mannitol. Their [2+2]-photocycloaddition to ethylene has been studied as a model reaction to evaluate the influence of the protecting groups of the central diol system on the facial diastereoselectivity. The trimethylsilyl derivative shows the highest selectivity. The bis-cyclobutane containing products have been converted into the enantiopure adducts of gamma-hydroxymethyl-alpha,beta-butenolide and ethylene. (C) 1999 Elsevier Science Ltd. All rights reserved.