(R)-2-[(diisopropoxyphosphoryl)methoxy]-3-hydroxypropyl p-toluenesulfonate | 1160512-81-1

• 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: (R)-2-[(diisopropoxyphosphoryl)methoxy]-3-hydroxypropyl p-toluenesulfonate
• 英文别名: diisopropyl (1R)-[2-hydroxy-1-(tosyloxymethyl)ethoxy]methylphosphonate
• CAS: 1160512-81-1
• 化学式: C₁₇H₂₉O₈PS
• 分子量: 424.452
• InChiKey: YJHIOQYKROXONA-MRXNPFEDSA-N

物化性质

• 沸点：
  559.9±50.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  27.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-2-[(diisopropoxyphosphoryl)methoxy]-3-hydroxypropyl p-toluenesulfonate 在 四(三苯基膦)钯 、 copper(I) 2-hydroxy-3-methylbenzoate 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 72.5h， 生成 6-(2R)-{2-[(diisopropoxyphosphoryl)methoxy]-3-hydroxypropoxy}-4-hydroxy-2-(4-hydroxyphenyl)pyrimidine
  参考文献：
  名称：

  利用Liebeskind-Srogl交叉偶联反应有效合成2-芳基嘧啶无环核苷膦酸酯

  摘要：

  使用Liebeskind-Srogl交叉偶联方案已制备了一系列带有连接在嘧啶部分C-2位置的各种芳基的新型无环核苷膦酸酯。研究和优化了高度官能化的2-（甲基硫烷基）嘧啶与各种芳基硼酸的反应。

  DOI：

  10.1016/j.tet.2011.07.040
• 作为产物：
  描述：

  diisopropyl (1R)-[2-benzyloxy-1-(tosyloxymethyl)ethoxy]-methylphosphonate 在 10% palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以81%的产率得到(R)-2-[(diisopropoxyphosphoryl)methoxy]-3-hydroxypropyl p-toluenesulfonate
  参考文献：
  名称：

  Acyclic nucleoside phosphonates with 5-azacytosine base moiety substituted in C-6 position

  摘要：

  Two methods for preparation of 6-substituted derivatives of anti DNA-viral agent 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine (HPMP-5-azaC) were developed: (1) ammonia mediated ring-opening reaction of diisopropyl esters of HPMP-5-azaC (4) to carbamoylguanidine derivatives followed by ring-closure reaction with orthoesters and (2) condensation reaction of 6-substituted 5-azacytosines with diisopropyl (1S)-[2-hydroxy-1-tosyloxymethyl)ethoxy]methylphosphonate (15). Deprotection of diisopropyl esters to free phosphonic acids was performed with bromotrimethylsilane in acetonitrile followed by hydrolysis. In contrast to parent compound HPMP-5-azaC, a substantial decrease of antiviral activity in case of 6-substituted analogues occurred. Surprisingly, N-3 isomer of 6-methyl-HPMP-5-azaC in the form of isopropyl ester revealed activity against RNA viruses (Sindbis virus). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.044

文献信息

• Acyclic nucleoside bisphosphonates: Synthesis and properties of chiral 2-amino-4,6-bis[(phosphonomethoxy)alkoxy]pyrimidines
  作者：Petra Doláková、Martin Dračínský、Milena Masojídková、Veronika Šolínová、Václav Kašička、Antonín Holý

  DOI：10.1016/j.ejmech.2008.09.031

  日期：2009.6

  2-Amino-4,6-bis[(phosphonomethoxy)alkoxy]pyrimidines bearing two equal or different achiral or chiral phosphonoalkoxy chains have been prepared either by aromatic nucleophilic substitution of 2-amino-4,6-dichloropyrimidine or by alkylation of 4,6-dihydroxy-2-(methylsulfanyl)pyrimidine with appropriate phosphonate-bearing building block. Alkylation of 4,6-dihydroxy-2-(methylsulfanyl)pyrimidine proved to be the method of choice for efficient preparation of variety of bisphosphonates. The enantiomeric purity of selected compounds was determined by capillary electrophoresis. Antiviral activity of bisphosphonates is discussed. (C) 2008 Elsevier Masson SAS. All rights reserved.