(dibenzyloxyphosphoryl)acetic acid benzyl ester | 214919-21-8

• 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: (dibenzyloxyphosphoryl)acetic acid benzyl ester
• 英文别名: benzyl (dibenzylphosphono)acetate；tribenzyl phosphonoacetate；Benzyl 2-bis(phenylmethoxy)phosphorylacetate；benzyl 2-bis(phenylmethoxy)phosphorylacetate
• CAS: 214919-21-8
• 化学式: C₂₃H₂₃O₅P
• 分子量: 410.406
• InChiKey: YMLQFUBSUDYNLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (dibenzyloxyphosphoryl)acetic acid benzyl ester 在 potassium tert-butylate 、 2-naphthalenesulphonyl azide 作用下， 以 甲苯 为溶剂， 反应 0.42h， 以68%的产率得到tribenzyl phosphonodiazoacetate
  参考文献：
  名称：

  Development of O–H insertion for the attachment of phosphonates to nucleosides; synthesis of α-carboxy phosphononucleosides

  摘要：

  Development of rhodium catalysed O-H insertion reactions employing alpha-diazophosphonates with appropriately protected adenosine, uridine and thymidine derivatives is described. This synthetic methodology leads, following deprotection, to novel phosphononucleoside derivatives bearing a carboxylic acid moiety adjacent to the phosphonate. Protection strategies are critical to the success of the key O-H insertion. There are two important aspects: avoiding competing insertion pathways or catalyst poisoning, and being able to achieve deprotection without degradation of the phosphononucleosides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.077
• 作为产物：
  描述：

  ethyl dibenzylphosphonoacetate 在 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (dibenzyloxyphosphoryl)acetic acid benzyl ester
  参考文献：
  名称：

  Development of O–H insertion for the attachment of phosphonates to nucleosides; synthesis of α-carboxy phosphononucleosides

  摘要：

  Development of rhodium catalysed O-H insertion reactions employing alpha-diazophosphonates with appropriately protected adenosine, uridine and thymidine derivatives is described. This synthetic methodology leads, following deprotection, to novel phosphononucleoside derivatives bearing a carboxylic acid moiety adjacent to the phosphonate. Protection strategies are critical to the success of the key O-H insertion. There are two important aspects: avoiding competing insertion pathways or catalyst poisoning, and being able to achieve deprotection without degradation of the phosphononucleosides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.077

文献信息

• Synthesis of Enzymatically Stable Analogues of GDP for Binding Studies with Transducin, the G-Protein of the Visual Photoreceptor
  作者：Stéphane Vincent、Sonya Grenier、Alain Valleix、Christian Salesse、Luc Lebeau、Charles Mioskowski

  DOI：10.1021/jo9806207

  日期：1998.10.1

  final deprotection step was achieved by catalytic hydrogenolysis. The biological properties of the compounds have been evaluated toward transducin, the G-protein of the visual photoreceptor. Three guanosine imidodiphosphate derivatives bearing a linker at different positions on the sugar and on the base were then prepared and evaluated, giving some insight into the GDP binding site of transducin.

  进行了五种鸟嘌呤二磷酸鸟嘌呤（GDP）的酶促稳定类似物的合成。焦磷酸部分依次被丙二酸酯，乙酰膦酸酯，膦酰基乙酸酯，亚甲基双膦酸酯和亚氨基二磷酸酯基团模拟。所有化合物都是通过合成一个瞬态完全保护的核苷二磷酸类似物来制备的，最后的脱保护步骤是通过催化氢解来实现的。已针对视觉感光器的G蛋白转导素评估了化合物的生物学特性。然后制备并评估了三种在糖上和碱基上不同位置带有连接子的鸟嘌呤亚氨基二磷酸衍生物，从而对转导蛋白的GDP结合位点有所了解。
• Reversible and Efficient Inhibition of UDP-Galactopyranose Mutase by Electrophilic, Constrained and Unsaturated UDP-Galactitol Analogues
  作者：Christophe Ansiaux、Inès N'Go、Stéphane P. Vincent

  DOI：10.1002/chem.201202302

  日期：2012.11.12

  A series of UDP‐galactitols were designed as analogues of high‐energy intermediates of the UDP‐galactopyranose mutase (UGM) catalyzed furanose/pyranose interconversion, an essential step of Mycobacterium tuberculosis cell wall biosynthesis. The final compounds structurally share the UDP and the galactitol substructures that were connected by four distinct electrophilic connections (epoxide, lactone

  设计了一系列UDP半乳糖类似物作为UDP半乳糖吡喃糖变位酶（UGM）催化呋喃糖/吡喃糖相互转化的高能中间体的类似物，这是结核分枝杆菌的重要步骤细胞壁生物合成。最终的化合物在结构上共有UDP和半乳糖醇亚结构，它们通过四个不同的亲电子连接（环氧化物，内酯和迈克尔受体）相连。所有分子均由常见的过苄基无环半乳糖前体合成，该前体通过烯基化，炔基化和环丙烷化作用衍生化。对UGM的抑制作用研究可以清楚地表明，UDP和半乳糖醇部分的相对方向发生细微变化会导致结合特性发生巨大变化。与已知的抑制剂相比，环氧化物衍生物显示出非常紧密的，可逆的抑制曲线。此外，一项与时间有关的失活研究表明，这些亲电子结构均不能与UGM或其FAD辅因子发生反应，
• [EN] 7-ARYL-3,9-DIAZABICYCLO(3.3.1)NON-6-ENE DERIVATIVES AND THEIR USE AS RENIN INHIBITORS IN THE TREATMENT OF HYPERTENSION, CARDIOVASCULAR OR RENAL DISEASES<br/>[FR] DERIVES DE 7-ARYL-3,9-DIAZABICYCLO(3.3.1)NON-6-ENE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE RENINE DANS LE TRAITEMENT DE L'HYPERTENSION, DE MALADIES CARDIOVASCULAIRES OU RENALES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2003093267A1

  公开（公告）日：2003-11-13

  The invention relates to novel 3,9-diazabicyclo[3.3.1]nonene derivatives of formula (I) and related compounds and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as inhibitors or renin.

  该发明涉及新型3,9-二氮杂双环[3.3.1]壬烯衍生物（I）及相关化合物，以及它们作为药物组合物中活性成分的用途。该发明还涉及相关方面，包括制备这些化合物的过程、含有这些化合物中的一个或多个的药物组合物，尤其是它们作为肾素抑制剂的用途。
• Cyclooctanone derivatives and cyclodecanone derivative, and use thereof
  申请人：——

  公开号：US20040082805A1

  公开（公告）日：2004-04-29

  The present invention provides a compound which has cytokine production inhibitory activity and is useful for the treatment of diseases which is associated with cytokine. The compound is represented by the following general formula (I) [wherein A represents a cyclic group which may be substituted; the partial structure -D E- represents a group represented by —CH 2 CH 2 — or —CH═CH—; W represents a group represented by —CH 2 —, —CH 2 CH 2 —, —CH═CH— or —CH═; the partial structure >X Y—represents a group represented by >CH—(CH 2 ) n —, >C═CH—, >CH—CH 2 —CH(OH)—, >CH—CH 2 —C(═O)—, >CH—O— or >CH—O—CO—, provided that when W is —CH═, then X Y— represents C—(CH 2 ) p —; Z represents a divalent aliphatic hydrocarbon group; R 1 and R 2 , which may be the same or different, each represents a hydrogen atom, or a hydroxyl, alkoxy or alkoxyalkoxy group; m is an integer of 0 or 1].

  本发明提供了一种具有细胞因子生产抑制活性的化合物，可用于治疗与细胞因子相关的疾病。该化合物由以下通式(I)表示：[其中，A表示可以被取代的环状基团；部分结构-DE-表示由—CH2CH2—或—CH═CH—表示的基团；W表示由—CH2—、—CH2CH2—、—CH═CH—或—CH═—表示的基团；部分结构>XY-表示由>CH—(CH2)n—、>C═CH—、>CH—CH2—CH(OH)—、>CH—CH2—C(═O)—、>CH—O—或>CH—O—CO—表示的基团，但当W为—CH═时，XY—表示C—(CH2)p—；Z表示二价的脂肪族碳氢基团；R1和R2，可以相同也可以不同，每个表示氢原子或羟基、烷氧基或烷氧基烷基；m是0或1的整数。]
• PYRROLIDINE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：Eisai Co., Ltd.

  公开号：EP1375479A1

  公开（公告）日：2004-01-02

  The present invention provides a compound which has cytokine production inhibitory activity and is useful for the treatment of diseases which is associated with cytokine. The compound is represented by the following general formula (I) [wherein A represents a cyclic group which may be substituted; the partial structure -D---E- represents a group represented by -CH2CH2- or -CH=CH-; W reprensents a group represented by -CH2-, - CHzCH2-, -CH=CH- or -CH=; the partial structure >X---Y- represents a group represented by >CH-(CH2)n-, >C=CH-, >CH-CH2-CH(OH)-, >CH-CH2-C (=O) -, >CH-O- or >CH-O-CO-, provided that when W is -CH=, then X---Y- represents C-(CH2)p-; Z represents a divalent aliphatic hydrocarbon group; R1 and R2, which may be the same or different, each represents a hydrogen atom, or a hydroxyl, alkoxy or alkoxyalkoxy group; m is an integer of 0 or 1] .

  本发明提供了一种化合物，它具有抑制细胞因子产生的活性，可用于治疗与细胞因子有关的疾病。该化合物由以下通式（I）表示[其中 A 代表可被取代的环状基团；部分结构-D--E-代表由-CH2CH2-或-CH=CH-代表的基团；W 代表由-CH2-、-CHzCH2-、-CH=CH-或-CH=；部分结构 >X---Y- 代表由 >CH-(CH2)n-、>C=CH-、>CH-CH2-CH(OH)-、>CH-CH2-C (=O) -、>CH-O- 或 >CH-O-CO- 所代表的基团，条件是当 W 为 -CH= 时，则 X---Y- 代表 C-(CH2)p-；Z 代表二价脂肪族烃基； R1 和 R2 可以相同或不同，各自代表氢原子或羟基、烷氧基或烷氧烷氧基； m 是 0 或 1 的整数]。