[bis(3-(hexadecyloxy)propoxy)phosphoryl]methyl tosylate | 959780-14-4

• 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: [bis(3-(hexadecyloxy)propoxy)phosphoryl]methyl tosylate
• 英文别名: bis(hexadecyloxypropyl) phosphonomethyltosylate；Bis(3-hexadecoxypropoxy)phosphorylmethyl 4-methylbenzenesulfonate；bis(3-hexadecoxypropoxy)phosphorylmethyl 4-methylbenzenesulfonate
• CAS: 959780-14-4
• 化学式: C₄₆H₈₇O₈PS
• 分子量: 831.232
• InChiKey: YVHLJDGNSRXYDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  56
• 可旋转键数：
  44
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [bis(3-(hexadecyloxy)propoxy)phosphoryl]methyl tosylate 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以93%的产率得到((3-(十六烷氧基)丙氧基)(羟基)磷酰基)甲基4-甲基苯磺酸酯
  参考文献：
  名称：

  Synthesis of phosphonomethoxyethyl or 1,3-bis(phosphonomethoxy)propan-2-yl lipophilic esters of acyclic nucleoside phosphonates

  摘要：

  A new alternative synthetic pathway towards mono and diesters of acyclic nucleoside phosphonates (PMEA, PMEC and PMEG) or [1,3-bis(phosphonomethoxy) propan-2-yl] adenine bearing one or two hexadecyloxypropyl ester groups (CH2)(3)O-n-C16H33 is reported. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.081
• 作为产物：
  描述：

  p-toluenesulfonyloxymethylphosphonic acid 在 吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 [bis(3-(hexadecyloxy)propoxy)phosphoryl]methyl tosylate
  参考文献：
  名称：

  Synthesis and antiviral activities of hexadecyloxypropyl prodrugs of acyclic nucleoside phosphonates containing guanine or hypoxanthine and a (S)-HPMP or PEE acyclic moiety

  摘要：

  Hexadecyloxypropyl esters of acyclic nucleoside phosphonates containing guanine (G) or hypoxanthine (Hx) and a (S)-[3-hydroxy-2-(phosphonomethoxy)propyl] [(S)-HPMP] or 2-(2-phosphonoethoxy)ethyl (PEE) acyclic moiety have been prepared. The activity of the prodrugs was evaluated in vitro against different virus families. Whereas ester derivatives of PEEHx and (S)-HPMPHx were antivirally inactive, monoesters of PEEG, and mono- and diesters of (S)-HPMPG showed pronounced antiviral activity against vaccinia virus and/or herpesviruses. Monoesters of (S)-HPMPG emerged as the most potent and selective derivatives against these DNA viruses. None of the compounds were inhibitory against RNA viruses and retroviruses. Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.027

文献信息

• Phosphonate Ester Derivatives and Methods of Synthesis Thereof
  申请人：Ware Roy W.

  公开号：US20120058976A1

  公开（公告）日：2012-03-08

  The disclosure describes methods of synthesis of phosphonate ester derivatives. Preferred methods according to the disclosure allow for large-scale preparation of phosphonate ester compounds having high purity. In some embodiments, preferred methods according to the disclosure also allow for the preparation of phosphonate ester derivatives without the use of chromatographic purification methods and in better yield than previously used methods for preparing such compounds. Also disclosed are morphic forms of phosphonate ester derivatives.

  该披露描述了合成膦酸酯衍生物的方法。根据该披露的首选方法允许大规模制备高纯度的膦酸酯化合物。在一些实施例中，根据该披露的首选方法还允许在比以往用于制备这类化合物的方法更好的产率下制备膦酸酯衍生物，而无需使用色谱纯化方法。还披露了膦酸酯衍生物的形态形式。
• PHOSPHONATE ESTER DERIVATIVES AND METHODS OF SYNTHESIS THEREOF
  申请人：Chimerix, Inc.

  公开号：US20150329575A1

  公开（公告）日：2015-11-19

  The disclosure describes methods of synthesis of phosphonate ester derivatives. Preferred methods according to the disclosure allow for large-scale preparation of phosphonate ester compounds having high purity. In some embodiments, preferred methods according to the disclosure also allow for the preparation of phosphonate ester derivatives without the use of chromatographic purification methods and in better yield than previously used methods for preparing such compounds. Also disclosed are morphic forms of phosphonate ester derivatives.

  本公开说明了合成膦酸酯衍生物的方法。根据公开说明，首选方法允许大规模制备高纯度的膦酸酯化合物。在某些实施例中，根据公开说明的首选方法还允许在不使用色谱纯化方法的情况下制备膦酸酯衍生物，并且比以前用于制备此类化合物的方法产量更高。此外，还公开了膦酸酯衍生物的形态形式。
• PHOSPHONATES WITH REDUCED TOXICITY FOR TREATMENT OF VIRAL INFECTIONS
  申请人：The Regents of the University of California

  公开号：EP2558466A2

  公开（公告）日：2013-02-20
• US8569321B2
  申请人：——

  公开号：US8569321B2

  公开（公告）日：2013-10-29
• US8846643B2
  申请人：——

  公开号：US8846643B2

  公开（公告）日：2014-09-30