[1-(Di-tert-butoxy-thiophosphoryloxymethyl)-3-(4-octyl-phenyl)-propyl]-carbamic acid tert-butyl ester | 949081-33-8

• 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: [1-(Di-tert-butoxy-thiophosphoryloxymethyl)-3-(4-octyl-phenyl)-propyl]-carbamic acid tert-butyl ester
• CAS: 949081-33-8
• 化学式: C₃₁H₅₆NO₅PS
• 分子量: 585.829
• InChiKey: WMLOWJCMQJPHHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.29
• 重原子数：
  39.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  66.02
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [1-(Di-tert-butoxy-thiophosphoryloxymethyl)-3-(4-octyl-phenyl)-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95%的产率得到1-dihydroxyphosphinothioyloxy-4-(4-octylphenyl)butan-2-amine;2,2,2-trifluoroacetic 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：

  1-苯基辛烷 在 四氮唑 、 盐酸 、 三乙基硅烷 、 三氯化铝 、 sodium ethanolate 、 四氯化钛 、 sulfur 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 33.0h， 生成 [1-(Di-tert-butoxy-thiophosphoryloxymethyl)-3-(4-octyl-phenyl)-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