dibenzyl tartrate | 896448-46-7

• 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: dibenzyl tartrate
• 英文别名: dibenzyl meso-tartrate；(+/-)-Weinsaeure-dibenzylester；meso-Weinsaeure-dibenzylester；dibenzyl (2R,3S)-2,3-dihydroxybutanedioate
• CAS: 896448-46-7
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: LCKIPSGLXMCAOF-IYBDPMFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dibenzyl tartrate 在 过碘酸 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成 苄基2-氧代乙酸酯
  参考文献：
  名称：

  Selection of a 2-azabicyclo[2.2.2]octane-based α4β1 integrin antagonist as an inhaled anti-asthmatic agent

  摘要：

  The alpha(4)beta(1) integrin, expressed on eosinophils and neutrophils, induces inflammation in the lung by facilitating cellular infiltration and activation. From a number of potent alpha(4)beta(1) antagonists that we evaluated for safety and efficacy, 1 was selected as a lead candidate for anti-asthma therapy by the inhalation route. We devised an optimized stereoselective synthesis to facilitate the preparation of a sufficiently large quantity of 1 for assessment in vivo. Administration of 1 to allergen-sensitive sheep by inhalation blocked the late-phase response of asthma and abolished airway hyper-responsiveness at 24 h following the antigen challenge. Additionally, the recruitment of inflammatory cells into the lungs was inhibited. Administration of 1 to ovalbumin-sensitized guinea pigs intraperitoneally blocked airway resistance and inhibited the recruitment of inflammatory cells. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.067
• 作为产物：
  描述：

  erythraric acid 、 苯甲醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以64%的产率得到dibenzyl tartrate
  参考文献：
  名称：

  二醇的选择性单酰化和二不对称Desymmetrization观-Tartrates使用2-吡啶基酯作为酰化剂和金属羧酸盐作为催化剂

  摘要：

  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。

  DOI：

  10.1021/acs.joc.9b00827

文献信息

• Hydrogenolysis of Benzyl Esters with Palladiumon-Carbon Catalysts
  作者：Harold L. Smith、Earle S. Brown、J. Doyle Smith、John Andrako

  DOI：10.1002/jps.2600540909

  日期：1965.9

  stereospecific sites on palladized charcoal hydrogenation catalysts have been made. The rates of hydrogenation of the benzyl esters of (+), (−), (±), and meso -tartaric acids, (±) malic acid, d -, l -, and dl -aspartic acids were measured. The rates were observed to be identical for the benzyl esters of the tartaric acids and the malic acid, indicating the possibility that these five substrates can utilize the

  进行了进一步的研究以证明在钯制木炭加氢催化剂上可能存在底物和立体特异性位点。测定了（+），（-），（±）和内消旋酒石酸，（±）苹果酸，d-，l-和dl-天冬氨酸的苄酯的氢化率。观察到酒石酸和苹果酸的苄基酯的速率相同，表明这五个底物可以利用相同的催化位点进行脱苄基作用的可能性。假定一个羟基和两个羰基苄氧基参与了催化剂-底物的复合物。当彼此比较时，二苄基天冬氨酸以相同的速率进行脱苄基作用。当与这些其他物质的速率相比时，发现琥珀酸二苄酯的氢解速率显着不同。不含羟基或氨基的琥珀酸二苄酯不会被期望利用与酒石酸，苹果酸和天冬氨酸的二苄酯相同的位点。
• SATURATED FUSED [1,2-b]PYRIDAZINONE COMPOUNDS
  申请人：Ruebsam Frank

  公开号：US20080214529A1

  公开（公告）日：2008-09-04

  The invention is directed to saturated fused [1,2-b]pyridazinone compounds and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.

  本发明涉及饱和融合[1,2-b]吡啶嗪化合物和含有这种化合物的制药组合物，其可用于治疗丙型肝炎病毒感染。
• 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。
• Selection of a 2-azabicyclo[2.2.2]octane-based α4β1 integrin antagonist as an inhaled anti-asthmatic agent
  作者：Edward C. Lawson、Rosemary J. Santulli、Alexey B. Dyatkin、Scott A. Ballentine、William M. Abraham、Sandra Rudman、Clive P. Page、Lawrence de Garavilla、Bruce P. Damiano、William A. Kinney、Bruce E. Maryanoff

  DOI：10.1016/j.bmc.2006.01.067

  日期：2006.6

  The alpha(4)beta(1) integrin, expressed on eosinophils and neutrophils, induces inflammation in the lung by facilitating cellular infiltration and activation. From a number of potent alpha(4)beta(1) antagonists that we evaluated for safety and efficacy, 1 was selected as a lead candidate for anti-asthma therapy by the inhalation route. We devised an optimized stereoselective synthesis to facilitate the preparation of a sufficiently large quantity of 1 for assessment in vivo. Administration of 1 to allergen-sensitive sheep by inhalation blocked the late-phase response of asthma and abolished airway hyper-responsiveness at 24 h following the antigen challenge. Additionally, the recruitment of inflammatory cells into the lungs was inhibited. Administration of 1 to ovalbumin-sensitized guinea pigs intraperitoneally blocked airway resistance and inhibited the recruitment of inflammatory cells. (c) 2006 Elsevier Ltd. All rights reserved.