[benzyloxy(bisbenzyloxyphosphorylmethyl)phosphinoylmethyl]phosphonic acid dibenzyl ester | 165271-66-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: [benzyloxy(bisbenzyloxyphosphorylmethyl)phosphinoylmethyl]phosphonic acid dibenzyl ester
• 英文别名: tetrabenzyl <<(benzyloxy)phosphoryl>bis(methylene)>bis(phosphonate)；bis(O,O'-dibenzyl phosphonomethyl)phosphinic acid benzyl ester；Bis[bis(phenylmethoxy)phosphorylmethyl]phosphoryloxymethylbenzene
• CAS: 165271-66-9
• 化学式: C₃₇H₃₉O₈P₃
• 分子量: 704.633
• InChiKey: LYEIKMBVUPFEFA-UHFFFAOYSA-N

物化性质

• 沸点：
  814.1±75.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [benzyloxy(bisbenzyloxyphosphorylmethyl)phosphinoylmethyl]phosphonic acid dibenzyl ester 在 三乙烯二胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以97%的产率得到<<(Benzyloxy)<<(benzyloxy)hydroxyphosphoryl>methyl>phosphoryl>methyl>phosphonic acid dibenzyl ester
  参考文献：
  名称：

  Selective Monodeprotection of Phosphate, Phosphite, Phosphonate, and Phosphoramide Benzyl Esters

  摘要：

  DOI：

  10.1021/jo00114a059
• 作为产物：
  描述：

  dibenzyl methaneselenophosphonate 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.03h， 生成 [benzyloxy(bisbenzyloxyphosphorylmethyl)phosphinoylmethyl]phosphonic acid dibenzyl ester
  参考文献：
  名称：

  酶和化学不可水解的二磷酸三核苷Ap（3）A和Gp（3）G的类似物的合成。

  摘要：

  二磷酸核苷是无处不在的化合物，与许多关键生物过程的调节密切相关。已经合成了该核苷酸家族的两个重要成员Ap（3）A和Gp（3）G的抗水解类似物。P（1），P（2）：P（2），P（3）-双-亚甲基二腺苷和双鸟苷三磷酸是使用原始方法从O，O-二烷基甲硒代膦酸酯制备的。尽管不能将甲烷膦酸根阴离子加成两倍到活化的磷物质上，但是锂化的甲烷硒酸膦酸根与亲电三价磷化合物的多重缩合被证明是非常有效的。一锅缩合/酯化/氧化序列涉及O，O-二烷基甲烷硒代膦酸酯提供了通往PCH（2）PCH（2）P主链的高效途径。

  DOI：

  10.1021/jo015836e

文献信息

• First Use of Benzyl Phosphites in theMichaelis-Arbuzov Reaction synthesis of mono-, Di-, and triphosphate analogs
  作者：Mourad Saady、Luc Lebeau、Charles Mioskowski

  DOI：10.1002/hlca.19950780314

  日期：1995.5.10

  Micaelis-Arbuzov reaction. Special experimental conditions allowed preparation of a set of phosphonate analogs of mono-, di-, and triphosphate. Furthermore, regioselective monodeprotection makes these molecules useful building blocks for the synthesis of analogs of polyphosphorylated compounds of biological interest (e.g. nucleotides), after removal of all phosphonate benzyl ester groups under very

  亚甲基苄基酯用于Micaelis-Arbuzov反应。特殊的实验条件允许制备一组单磷酸，二磷酸和三磷酸的膦酸酯类似物。此外，在非常温和的条件下以高收率除去所有膦酸酯苄酯基团之后，区域选择性单脱保护使这些分子成为合成具有生物学意义的多磷酸化化合物（例如核苷酸）的类似物的有用组成部分。
• An Unsymmetrical Approach to the Synthesis of Bismethylene Triphosphate Analogues
  作者：Scott D. Taylor、Farzad Mirzaei、Stephen L. Bearne

  DOI：10.1021/ol0615432

  日期：2006.9

  A protected, unsymmetrical bismethylene triphosphate analogue was prepared by sequential Michaelis-Arbuzov reactions on ethyl bis(halomethyl) phosphinates. This species was monodeprotected at one of the terminal phosphonate groups in high yield. The resulting monodeprotected compound was used to achieve the first syntheses of the bismethylene triphosphate analogues of UTP and CTP.
• Synthesis of Di- and Triphosphate Ester Analogs via a Modified Michaelis-Arbuzov Reaction
  作者：M Saady

  DOI：10.1016/00404-0399(50)10097-

  日期：1995.7.17
• Selenophosphonates as building blocks for the preparation of bis-methylene analogs of triphosphates
  作者：Stéphane Mons、Emmanuel Klein、Charles Mioskowski、Luc Lebeau

  DOI：10.1016/s0040-4039(01)01088-7

  日期：2001.8

  A new route to bis-methylene analogs of triphosphate esters involving carbanion chemistry is described. Lithiated methaneselenophosphonate anion is condensed several times with chlorophosphites and phosphoramidous chlorides prior to esterification/transesterification and selenation or oxidation. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of Stable Analogues of Thiamine Di- and Triphosphate as Tools for Probing a New Phosphorylation Pathway
  作者：Emmanuel Klein、Hoàng-Oanh Nghiêm、Alain Valleix、Charles Mioskowski、Luc Lebeau

  DOI：10.1002/1521-3765(20021018)8:20<4649::aid-chem4649>3.0.co;2-m

  日期：2002.10.18

  Thiamine (vitamin B1) is an essential nutritional factor metabolized inside the body in its mono-, di-, and triphosphate forms. Although the action of thiamine and thiamine diphosphate have been intensely investigated, many questions remain unanswered and the role of thiamine triphosphate is still especially unknown. To probe recent hypotheses on the implication of thiamine triphosphate in a new phosphorylation pathway involving synaptic proteins, we synthesized a series of thiamine di- and triphosphate analogues that are resistant to both enzymatic and chemical hydrolyses. The key step in the preparation of the title compounds is the coupling of thiamine propyl disulfide with adequately protected methylenebisphosphonic acid, the corresponding triphosphate analogue, and difluoromethylenebisphosphonic acid.