Phosphorous acid diethyl ester (1S,2S,3R,4R,5R,6S)-2,4,5-tris-(diethoxy-phosphanyloxy)-3,6-dimethoxy-cyclohexyl ester | 651313-66-5

• 英文名称: Phosphorous acid diethyl ester (1S,2S,3R,4R,5R,6S)-2,4,5-tris-(diethoxy-phosphanyloxy)-3,6-dimethoxy-cyclohexyl ester
• CAS: 651313-66-5
• 化学式: C₂₄H₅₂O₁₄P₄
• 分子量: 688.564
• InChiKey: APDKTMXYXVLIJK-MQLGOCQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  42.0
• 可旋转键数：
  26.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  129.22
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Phosphorous acid diethyl ester (1S,2S,3R,4R,5R,6S)-2,4,5-tris-(diethoxy-phosphanyloxy)-3,6-dimethoxy-cyclohexyl ester 在 叔丁基过氧化氢 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以0.286 g的产率得到2,5-di-O-methyl-1,3,4,6-tetrakis(diethoxyphospho)-myo-inositol
  参考文献：
  名称：

  Synthesis of potent Ins(1,4,5)P3 5-phosphatase inhibitors by modification of myo-inositol 1,3,4,6-tetrakisphosphate

  摘要：

  Three myo-inositol tetrakisphosphate analogues were synthesised based upon myo-inositol 1,3,4,6-tetrakisphosphate: 2,5-di-O-methyl myo-inositol-1,3,4,6-tetrakisphosphate 19 and its phosphorothioate derivative 22, together with myo-inositol 1,3,4,6 tetrakisphosphorothioate 25. These compounds were prepared by phosphitylating 2,5-di-0-methyl-myo-inositol and 2,5-di-O-benzyl-myo-inositol followed by oxidation with t-butylhydroperoxide or sulfoxidation at room temperature using sulfur in a mixed solvent of DMF and pyridine. Sulfoxidation was complete within 15 min; however, without DMF, the reaction was much slower, and required overnight. When evaluated against Ins(1,4,5)P-3 5-phosphatase, 3-kinase and for Ca2+ release at the Ins(1,4,5)P3 receptor, only weak activity was observed for Ca2+ release. 22 and 25 are potent 5-phosphatase inhibitors and 25 is a moderate inhibitor of 3-kinase. Thus, we have synthesised potent enzyme inhibitors, which do not mobilise Ca2+ and devised conditions for quick, clean and inexpensive sulfoxidation of inositol polyphosphite intermediates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00347-x
• 作为产物：
  描述：

  DL-1,4-di-O-allyl-3,6-di-O-p-methoxybenzyl-2,5-di-O-methyl-myo-inositol 在 palladium on activated charcoal 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.75h， 生成 Phosphorous acid diethyl ester (1S,2S,3R,4R,5R,6S)-2,4,5-tris-(diethoxy-phosphanyloxy)-3,6-dimethoxy-cyclohexyl ester
  参考文献：
  名称：

  Synthesis of potent Ins(1,4,5)P3 5-phosphatase inhibitors by modification of myo-inositol 1,3,4,6-tetrakisphosphate

  摘要：

  Three myo-inositol tetrakisphosphate analogues were synthesised based upon myo-inositol 1,3,4,6-tetrakisphosphate: 2,5-di-O-methyl myo-inositol-1,3,4,6-tetrakisphosphate 19 and its phosphorothioate derivative 22, together with myo-inositol 1,3,4,6 tetrakisphosphorothioate 25. These compounds were prepared by phosphitylating 2,5-di-0-methyl-myo-inositol and 2,5-di-O-benzyl-myo-inositol followed by oxidation with t-butylhydroperoxide or sulfoxidation at room temperature using sulfur in a mixed solvent of DMF and pyridine. Sulfoxidation was complete within 15 min; however, without DMF, the reaction was much slower, and required overnight. When evaluated against Ins(1,4,5)P-3 5-phosphatase, 3-kinase and for Ca2+ release at the Ins(1,4,5)P3 receptor, only weak activity was observed for Ca2+ release. 22 and 25 are potent 5-phosphatase inhibitors and 25 is a moderate inhibitor of 3-kinase. Thus, we have synthesised potent enzyme inhibitors, which do not mobilise Ca2+ and devised conditions for quick, clean and inexpensive sulfoxidation of inositol polyphosphite intermediates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00347-x