[(1R,2S)-2-(Di-tert-butoxy-thiophosphoryloxy)-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester | 949081-36-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(1R,2S)-2-(Di-tert-butoxy-thiophosphoryloxy)-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester
• CAS: 949081-36-1
• 化学式: C₃₁H₅₅N₂O₆PS
• 分子量: 614.827
• InChiKey: OJGYIVYEUHRITI-JYFHCDHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.68
• 重原子数：
  41.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  95.12
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [(1R,2S)-2-(Di-tert-butoxy-thiophosphoryloxy)-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 、 三氟乙酸 在 三甲基溴硅烷 、 苯硫酚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以94%的产率得到Thiophosphoric acid O-[(1S,2R)-2-amino-1-methyl-2-(4-octyl-phenylcarbamoyl)-ethyl] ester; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis, stability, and implications of phosphothioate agonists of sphingosine-1-phosphate receptors

  摘要：

  Phosphothioates may provide metabolic stability when compared to their phosphate counterparts, while retaining the potency and efficacy as agonists at sphingosine-1 -phosphate (SIP) G-protein coupled receptors. Unlike their phosphate precursors, phosphothioate compounds with SIP-receptor profiles similar to that of FTY720, an emerging immunomodulator, were shown to evoke prolonged lymphopenia in vivo. Analysis of mouse plasma concentrations for a series of related alcohol/phosphate/phosphothioate compounds showed the conversion of the phosphate to alcohol. These preliminary data highlight the importance of metabolic regulation of SIP receptor ligands. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.057
• 作为产物：
  描述：

  Boc-O-benzyl-D-threonine 在 palladium on activated charcoal 四氮唑 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 sulfur 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 [(1R,2S)-2-(Di-tert-butoxy-thiophosphoryloxy)-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis, stability, and implications of phosphothioate agonists of sphingosine-1-phosphate receptors

  摘要：

  Phosphothioates may provide metabolic stability when compared to their phosphate counterparts, while retaining the potency and efficacy as agonists at sphingosine-1 -phosphate (SIP) G-protein coupled receptors. Unlike their phosphate precursors, phosphothioate compounds with SIP-receptor profiles similar to that of FTY720, an emerging immunomodulator, were shown to evoke prolonged lymphopenia in vivo. Analysis of mouse plasma concentrations for a series of related alcohol/phosphate/phosphothioate compounds showed the conversion of the phosphate to alcohol. These preliminary data highlight the importance of metabolic regulation of SIP receptor ligands. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.057