O,O′-bis(3,5-di-tert-butylbenzoyl) dibenzyl (2R,3R)-tartrate | 1400275-70-8

• 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: O,O′-bis(3,5-di-tert-butylbenzoyl) dibenzyl (2R,3R)-tartrate
• 英文别名: (R,R)-dibenzyl tartrate di-3,5-di-tert-butylbenzoate
• CAS: 1400275-70-8
• 化学式: C₄₈H₅₈O₈
• 分子量: 762.984
• InChiKey: JWTPNGMNSDASTO-XRSDMRJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.11
• 重原子数：
  56.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  O,O′-bis(3,5-di-tert-butylbenzoyl) dibenzyl (2R,3R)-tartrate 在 10% Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以100%的产率得到(2R,3R)-2,3-bis[(3,5-ditert-butylbenzoyl)oxy]butanedioic acid
  参考文献：
  名称：

  Identification of a Foldaxane Kinetic Byproduct during Guest-Induced Single to Double Helix Conversion

  摘要：

  An aromatic oligoamide sequence was designed and synthesized to fold in a single helix having a large cavity and to behave as a host for a dumbbell-shaped guest derived from tartaric acid. NMR, molecular modeling, and circular dichroism (CD) evidence demonstrated the rapid formation of this 1:1 host-guest complex and induction of the helix handedness of the host by the guest. This complex was found to be a long-lived kinetic supramolecular byproduct, as it slowly transformed into a 2:2 host-guest complex with two guest molecules bound at the extremities of a double helix formed by the host, as shown by NMR and CD spectroscopy and a solid-state structure. The guest also induced the handedness of the double helical host, but with an opposite bias. The chiroptical properties of the system were thus found to revert with time as the 1:1 complex formed first, followed by the 2:2 complex.

  DOI：

  10.1021/ja3064364
• 作为产物：
  描述：

  3,5-二叔丁基苯甲酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 O,O′-bis(3,5-di-tert-butylbenzoyl) dibenzyl (2R,3R)-tartrate
  参考文献：
  名称：

  Identification of a Foldaxane Kinetic Byproduct during Guest-Induced Single to Double Helix Conversion

  摘要：

  An aromatic oligoamide sequence was designed and synthesized to fold in a single helix having a large cavity and to behave as a host for a dumbbell-shaped guest derived from tartaric acid. NMR, molecular modeling, and circular dichroism (CD) evidence demonstrated the rapid formation of this 1:1 host-guest complex and induction of the helix handedness of the host by the guest. This complex was found to be a long-lived kinetic supramolecular byproduct, as it slowly transformed into a 2:2 host-guest complex with two guest molecules bound at the extremities of a double helix formed by the host, as shown by NMR and CD spectroscopy and a solid-state structure. The guest also induced the handedness of the double helical host, but with an opposite bias. The chiroptical properties of the system were thus found to revert with time as the 1:1 complex formed first, followed by the 2:2 complex.

  DOI：

  10.1021/ja3064364

文献信息

• Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl <i>meso</i>-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts
  作者：Yuki Hashimoto、Chiaki Michimuko、Koki Yamaguchi、Makoto Nakajima、Masaharu Sugiura

  DOI：10.1021/acs.joc.9b00827

  日期：2019.7.19

  as a catalyst, 1,2-diols, 1,3-diols, and catechol were selectively monoacylated. Furthermore, the highly enantioselective desymmetrization of meso-tartrates was achieved for the first time, utilizing 2-pyridyl esters and NiBr2/AgOPiv/Ph-BOX in CH3CN or CuCl2/AgOPiv/Ph-BOX in EtOAc catalyst systems (up to 96% ee). The latter catalyst system was also effective for the kinetic resolution of dibenzyl dl-tartrate

  用2-吡啶基苯甲酸酯作为酰化剂和Zn（OAc）2作为催化剂，1,2-二醇，1,3-二醇和邻苯二酚被选择性地单酰化。此外，首次实现了酒石酸内消旋酒石酸酯的高对映选择性去对称化，这是通过在CH 3 CN中使用2-吡啶基酯和NiBr 2 / AgOPiv / Ph-BOX或在EtOAc催化剂体系中使用CuCl 2 / AgOPiv / Ph-BOX来实现的（对等）到96％ee）。后者的催化剂体系，也是有效的苄动力学拆分DL -酒石酸盐。