tris-(tetra-n-butylammonium)thiolodiphosphate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: tris-(tetra-n-butylammonium)thiolodiphosphate
• 英文别名: tris(tetra-N-butylammonium) thiodiphosphate；tris(tetrabutylammonium) thiopyrophosphate；tris(tetra-n-butylammonium) thiopyrophosphate；tris-(tetra-n-butylammonium)thiodiphosphate；tris(tetra-n-butylammonium) hydrogenthiopyrophosphate
• 化学式: 3C₁₆H₃₆N*HO₆P₂S
• 分子量: 918.423
• InChiKey: MHGXRACWJWNIBY-UHFFFAOYSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  26.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  109.72
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-4-(Tetrahydropyran-2-yloxy)-3-methylbut-2-enylchloride 、 tris-(tetra-n-butylammonium)thiolodiphosphate 以 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  WO2007/99117

  摘要：

  公开号：
• 作为产物：
  描述：

  四丁基氢氧化铵 在 O,O,O',S-tetrakis(trimethylsilyl) thiodiphosphate 作用下， 以 水 、 乙腈 为溶剂， 以5.36 g的产率得到tris-(tetra-n-butylammonium)thiolodiphosphate
  参考文献：
  名称：

  Synthesis of (S)-Isoprenoid Thiodiphosphates as Substrates and Inhibitors

  摘要：

  Thiolo thiophosphate analogues of isopentenyl diphosphate (IPP), dimethylallyl. diphosphate (DMAPP), geranyl diphosphate (GPP), farnesyl diphosphate (FPP), and geranylgeranyl diphosphate (GGPP) were synthesized, Inorganic thiopyrophosphate (SPP) was prepared from trimethyl phosphate in four steps. The tris(tetra-n-butylammonium) salt was then used to convert isopentenyl tosylate to (S)-isopentenyl thiodiphosphate (ISPP). (S)-Dimethylallyl (DMASPP), (S)-geranyl (GSPP), (S)-farnesyl (FSPP), and (S)-geranylgeranyl thiodiphosphate (GGSPP) were prepared from the corresponding bromides in a similar manner. ISPP and GSPP were substrates for avian farnesyl diphosphate synthase (FPPase). Incubation of the enzyme with ISPP and GPP gave FSPP, whereas incubation with IPP and GSPP gave FPP. GSPP was a substantially less reactive than GPP in the chain elongation reaction and was an excellent competitive inhibitor, K-I(GSPP) = 24.8 muM, of the enzyme. Thus, when ISPP and DMAPP were incubated with FPPase, GSPP accumulated and was only slowly converted to FSPP.

  DOI：

  10.1021/jo010505n
• 作为试剂：
  描述：

  4-氯丁醇 在 吡啶 、 C₁₃H₁₀ClO₂PolS 、 tris-(tetra-n-butylammonium)thiolodiphosphate 、 碳酸氢铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 异丙醇 为溶剂， 反应 48.0h， 以61%的产率得到trisodium S-(4-chlorobutyl) thiodiphosphate
  参考文献：
  名称：

  WO2007/99117

  摘要：

  公开号：

文献信息

• Thiopyrophosphoantigens: Solid-phase Synthesis and in Vitro Characterization of a New Class of Vγ9 Vδ2 T Cells Activators
  作者：Perla Breccia、Francesca Angeli、Ilaria Cerbara、Alessandra Topai、Giovanni Auricchio、Angelo Martino、Vittorio Colizzi、Fabrizio Poccia

  DOI：10.1021/jm900054u

  日期：2009.6.25

  The V gamma 9 V delta 2 T cells mediate rapid, innate-like immune responses to pathogens and are important in several key immunoregulatory pathways, including those involved in infections and tumor development. V gamma 9 V delta 2 T cells respond to low molecular weight isoprenoid phosphoantigens; the prototypic stimulatory compound is isopentenylpyrophosphate (IPP), an alkylphosphate intermediate of mevalonate metabolism that elicits proliferative, cytotoxic, and cytokine secretion responses. We studied the replacement of the pyrophosphate moiety with the thiopyrophosphate bioisostere, synthesizing thioanalogues of IPP and 4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMBPP, the most potent natural antigen known to date). Once their in vitro efficacy and stability had been demonstrated, we synthesized a small library of compounds through the development of an innovative solid-phase strategy. Biological results confirmed thioHMBPP to be the best compound of this first series. Future aims are (i) the exploitation of the parallel solid-phase strategy to further explore structure-activity relationships of this new class of synthetic antigens and (ii) the determination of the PK/PD profile of thioHMBPP.
• Synthesis of Geranyl <i>S</i>-Thiolodiphosphate. A New Alternative Substrate/Inhibitor for Prenyltransferases
  作者：Richard M. Phan、C. Dale Poulter

  DOI：10.1021/ol006055n

  日期：2000.7.1

  [GRAPHICS]The tris(tetra-n-butylammonium) salt of thiopyrophosphate 5 was prepared from trimethyl phosphate in four steps. Treatment of geranyl bromide with 5 gave an 80% yield of geranyl S-thiolodiphosphate (6), Thiolodiphosphate 6 is substantially less reactive than geranyl diphosphate (7) in the prenyl transfer reaction catalyzed by farnesyl diphosphate synthase and is a good inhibitor of the enzyme.