[(3R)-4-bromo-3-hydroxy-3-methylbutyl] phosphono hydrogen phosphate;N,N'-dibenzylethane-1,2-diamine | 1399853-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: [(3R)-4-bromo-3-hydroxy-3-methylbutyl] phosphono hydrogen phosphate;N,N'-dibenzylethane-1,2-diamine
• CAS: 1399853-65-6
• 化学式: C₅H₁₃BrO₈P₂*C₁₆H₂₀N₂
• 分子量: 583.353
• InChiKey: PIKUFVOWMCTIRZ-QDXATWJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl 4-methylbenzene­sulfonate 在 4-二甲氨基吡啶 、 ammonium cerium (IV) nitrate 、 三甲基溴硅烷 、 4-甲基苯磺酸吡啶 、 caesium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 氘代甲醇-d 、 氯仿 、 水 、 丙酮 、 乙腈 为溶剂， 反应 82.5h， 生成 [(3R)-4-bromo-3-hydroxy-3-methylbutyl] phosphono hydrogen phosphate;N,N'-dibenzylethane-1,2-diamine
  参考文献：
  名称：

  Synthesis of phosphoantigens: Scalable accesses to enantiomers of BrHPP and studies on N-HDMAPP synthesis

  摘要：

  Phosphoantigens enable the access to a new anti-tumoral and anti-infectious therapeutic pathway, based on innate immunity through the selective activation of T beta 9 delta 2 lymphocytes. The first proof of concept of this new immunotherapy approach was demonstrated with the synthetic phosphoantigen named bromohydrin pyrophosphate (BrHPP, IPH 1101) which was administrated in racemic form to about 200 patients in six clinical trials with good safety and promising early signals of efficacy in type C viral hepatitis and follicular non-Hodgkin's lymphoma. Enantiopure samples of BrHPP in gram scale are required for further studies on structure-bioactivity relationship. Thus we developed two complementary synthetic pathways, the first using transformation of a chiral compound and the second involving asymmetric synthesis starting from a prochiral building-block. The synthesis of a second-generation phosphoantigen, N-HDMAPP, which bears a phosphoramidate moiety, was also investigated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.092

文献信息

• Synthesis of phosphoantigens: Scalable accesses to enantiomers of BrHPP and studies on N-HDMAPP synthesis
  作者：Delphine Brégeon、Laurent Ferron、Antony Chrétien、Frédéric Guillen、Viacheslav Zgonnik、Marion Rivaud、Marie-Rose Mazières、Gérard Coquerel、Christian Belmant、Jean-Christophe Plaquevent

  DOI：10.1016/j.bmcl.2012.07.092

  日期：2012.9

  Phosphoantigens enable the access to a new anti-tumoral and anti-infectious therapeutic pathway, based on innate immunity through the selective activation of T beta 9 delta 2 lymphocytes. The first proof of concept of this new immunotherapy approach was demonstrated with the synthetic phosphoantigen named bromohydrin pyrophosphate (BrHPP, IPH 1101) which was administrated in racemic form to about 200 patients in six clinical trials with good safety and promising early signals of efficacy in type C viral hepatitis and follicular non-Hodgkin's lymphoma. Enantiopure samples of BrHPP in gram scale are required for further studies on structure-bioactivity relationship. Thus we developed two complementary synthetic pathways, the first using transformation of a chiral compound and the second involving asymmetric synthesis starting from a prochiral building-block. The synthesis of a second-generation phosphoantigen, N-HDMAPP, which bears a phosphoramidate moiety, was also investigated. (C) 2012 Elsevier Ltd. All rights reserved.