<<(Benzyloxy)<<(benzyloxy)hydroxyphosphoryl>methyl>phosphoryl>methyl>phosphonic acid dibenzyl ester | 165271-67-0

• 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)<<(benzyloxy)hydroxyphosphoryl>methyl>phosphoryl>methyl>phosphonic acid dibenzyl ester
• 英文别名: tribenzyl hydrogen <<(benzyloxy)phosphoryl>bis(methylene)>bis(phosphonate)；[Bis(phenylmethoxy)phosphorylmethyl-phenylmethoxyphosphoryl]methyl-phenylmethoxyphosphinic acid
• CAS: 165271-67-0
• 化学式: C₃₀H₃₃O₈P₃
• 分子量: 614.509
• InChiKey: HARRNNXIQWAPOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  齐多夫定 、 <<(Benzyloxy)<<(benzyloxy)hydroxyphosphoryl>methyl>phosphoryl>methyl>phosphonic acid dibenzyl ester 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以51%的产率得到
  参考文献：
  名称：

  Synthesis of haptens for the development of a solid-phase immobilized epitope-immunoassay (SPIE-IA) of AZT-TP

  摘要：

  The synthesis of the reduced form of AZT-triphosphate, 3'-amino-3'-deoxythymidine-5'-triphosphate, and of its stable analog, 3'-amino-3'-deoxythymidine-5'-(alpha;beta:beta,gamma-bis-methylene)triphosphate, is described. AMT-TP and AMT-PCPCP were prepared to develop a specific immunometric assay for AZT-TP. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00785-6
• 作为产物：
  描述：

  亚磷酸三苄酯 在 三乙烯二胺 作用下， 以 苯 为溶剂， 60.0~155.0 ℃ 、6.67 Pa 条件下， 反应 22.0h， 生成 <<(Benzyloxy)<<(benzyloxy)hydroxyphosphoryl>methyl>phosphoryl>methyl>phosphonic acid dibenzyl ester
  参考文献：
  名称：

  An Unsymmetrical Approach to the Synthesis of Bismethylene Triphosphate Analogues

  摘要：

  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.

  DOI：

  10.1021/ol0615432

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。
• Selective Monodeprotection of Phosphate, Phosphite, Phosphonate, and Phosphoramide Benzyl Esters
  作者：Mourad Saady、Luc Lebeau、Charles Mioskowski

  DOI：10.1021/jo00114a059

  日期：1995.5
• Synthesis of Polyphosphorylated AZT Derivatives for the Development of Specific Enzyme Immunoassays
  作者：Thierry Brossette、Anne Le Faou、Laure Goujon、Alain Valleix、Christophe Créminon、Jacques Grassi、Charles Mioskowski、Luc Lebeau

  DOI：10.1021/jo982502p

  日期：1999.7.1

  The synthesis of a series of analogues of the different polyphosphorylated metabolites of AZT has been carried out. The compounds were designed in order to raise specific antibodies for the development of highly sensitive titration kits for the intracellular metabolites of AZT. The pyrophosphate moiety in AZT-DP and AZT-TP analogues is mimicked by the methylene bisphosphonate group to provide in vivo stability of the compounds. An omega-amino linker was introduced at the N-3 position on the base to allow the further anchoring of the compounds to a carrier protein before immunization, tentitatively focusing the specificity of the immune response toward the phosphate mimic moiety and the nonnatural sugar.
• Synthesis of a non-hydrolyzable AZT-triphosphate analogue designed for the production of anti-AZT-TP antibodies
  作者：Thierry Brossette、Alain Valleix、Laure Goujon、Christophe Cre´minon、Jacques Grassi、Charles Mioskowski、Luc Lebeau

  DOI：10.1016/s0040-4039(99)00497-9

  日期：1999.4

  An enzymatically stable analogue of AZT-triphosphate is prepared in 7 steps starting from thymidine. The thymine moiety is Functionalized at N-3 to allow the Further cross-linking to a carrier protein for subsequent immunization of rabbits in order to raise specific antibodies directed against AZT-TP. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.