O-(2,5-二氯苯基)硫代二氯磷酸酯 | 87668-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: O-(2,5-二氯苯基)硫代二氯磷酸酯
• 中文别名: 2-(2-羟基丙氧基)-1-甲基乙基油酸酯
• 英文名称: 2,5-dichlorophenyl phosphorodichloridothioate
• 英文别名: dichlorothiophosphoric acid O-(2,5-dichloro-phenyl ester)；Dichlorothiophosphorsaeure-O-(2,5-dichlor-phenylester)；dichloro-(2,5-dichlorophenoxy)-sulfanylidene-λ5-phosphane
• CAS: 87668-61-9
• 化学式: C₆H₃Cl₄OPS
• 分子量: 295.941
• InChiKey: SZENMFRIUYOZQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-(2,5-二氯苯基)硫代二氯磷酸酯 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.25h， 生成
  参考文献：
  名称：

  Water-soluble cholesteryl-containing phosphorothioate monogalactosides: synthesis, properties, and use in lowering blood cholesterol by directing plasma lipoproteins to the liver

  摘要：

  The synthesis of several monogalactoside-terminated phosphorothiolated cholesteryl derivatives is described. Monogalactosyl derivatives are coupled by phosphorothiolation to cholesterol by using ethylene glycol units as hydrophilic spacer moieties. The resulting compounds are easily soluble in water. Upon addition of such solutions to human serum (to 2 mM final concentration) the compounds are readily incorporated into lipoproteins. Isolated low-density lipoprotein (LDL) and high-density lipoprotein (HDL), preloaded with the compounds, are rapidly cleared from the circulation by the liver. The hepatic association is blocked by N-acetylgalactosamine, which indicates that galactose-specific recognition sites are responsible for the increased liver uptake. The plasma clearance and hepatic uptake of LDL loaded with the compounds is substantially higher (about 2-fold) than clearance and uptake of HDL containing the compounds. The selectivity of the effects of monogalactoside-terminated phosphorothiolated cholesteryl derivatives on the in vivo behavior of LDL as compared to that of HDL indicates that these compounds might be used to lower specifically LDL levels in patients with a high LDL-cholesterol level.

  DOI：

  10.1021/jm00107a024
• 作为产物：
  描述：

  2,5-二氯苯酚 在 三氯硫磷 、 三氯化磷 作用下， 生成 O-(2,5-二氯苯基)硫代二氯磷酸酯
  参考文献：
  名称：

  Aromatic Phosphorodichloridites and Phosphorodichloridothioates. I. Aryl Phosphorodichloridites

  摘要：

  DOI：

  10.1021/jo01105a025

文献信息

• Use of 2,5-dichlorophenyl phosphorodichloridothioate in the synthesis of diastereoisomeric dinucleoside phosphorothioates
  作者：�znur Kemal、Colin B. Reese、Halina T. Serafinowska

  DOI：10.1039/c39830000591

  日期：——

  A convenient method for the synthesis, by the phosphotriester approach, of dinucleoside phosphorothioates is illustrated by the preparation and isolation of the pure Rp- and Sp-diastereoisomers of thymidine-3′ thymidine-5′ phosphorothioate (5).

  通过制备和分离胸苷-3'胸苷-5'硫代磷酸酯的纯R p-和S p-非对映异构体，说明了通过磷酸三酯方法合成二核苷硫代磷酸酯的简便方法（5）。
• Synthesis of oligonucleotides
  申请人：Avecia Limited

  公开号：EP1325927A2

  公开（公告）日：2003-07-09

  A process for the synthesis in solution phase of a phosphorothioate triester is provided. The process comprises the solution phase coupling of an H-phosphonate with an alcohol in the presence of a coupling agent to form an H-phosphonate diester. The H-phosphonate diester is oxidised in situ with a sulfur transfer agent to produce the phosphorothioate triester. Preferably, the H-phosphonate and alcohol are protected nucleosides or oligonucleotides. Oligonucleotide H-phosphonates which can be used in the formation of phosphorothioate triesters are also provided.

  本发明提供了一种在溶液相中合成硫代磷酸酯三酯的工艺。该工艺包括在偶联剂存在下，将 H-膦酸盐与醇进行溶液相偶联，形成 H-膦酸盐二酯。H-phosphonate 二酯与硫转移剂原位氧化，生成硫代磷酸酯三酯。H-phosphonate 和醇最好是受保护的核苷或寡核苷酸。还提供了可用于形成硫代磷酸三酯的寡核苷酸 H-膦酸盐。
• Solution phase synthesis of oligonucleotides
  申请人：Avecia Limited

  公开号：US20030083490A1

  公开（公告）日：2003-05-01

  A process for the synthesis in solution phase of a phosphorothioate triester is provided. The process comprises the solution phase coupling of an H-phosphonate with an alcohol in the presence of a coupling agent to form an H-phosphonate diester. The H-phosphonate diester is oxidised in situ with a sulfur transfer agent to produce the phosphorothioate triester. Preferably, the H-phosphonate and alcohol are protected nucleosides or oligonucleotides. Oligonucleotide H-phosphonates which can be used in the formation of phosphorothioate triesters are also provided.

  本发明提供了一种在溶液相中合成硫代磷酸酯三酯的工艺。该工艺包括在偶联剂存在下，将 H-膦酸盐与醇进行溶液相偶联，形成 H-膦酸盐二酯。H-phosphonate 二酯与硫转移剂原位氧化，生成硫代磷酸酯三酯。H-phosphonate 和醇最好是受保护的核苷或寡核苷酸。还提供了可用于形成硫代磷酸三酯的寡核苷酸 H-膦酸盐。
• Method for the manufacture of o-aryl o-lower alkyl phosphorochloridothioates
  申请人：DOW CHEMICAL CO

  公开号：US02887506A1

  公开（公告）日：1959-05-19
• SOLUTION PHASE SYNTHESIS OF OLIGONUCLEOTIDES
  申请人：Avecia Limited

  公开号：EP1003758B1

  公开（公告）日：2003-04-09