Methanesulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-4-methanesulfonyloxy-2-methyl-butyl ester | 756836-67-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-4-methanesulfonyloxy-2-methyl-butyl ester
• CAS: 756836-67-6
• 化学式: C₁₃H₃₀O₇S₂Si
• 分子量: 390.595
• InChiKey: AMOVKGVJIFHVBY-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  95.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-4-methanesulfonyloxy-2-methyl-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.0h， 生成 (R)-epoxide of isopentenyl diphosphate
  参考文献：
  名称：

  Synthesis of chiral phosphoantigens and their activity in γδ T cell stimulation

  摘要：

  gammadelta T cells expressing Vgamma2Vdelta2 T cell receptors are activated by a broad range of phosphorus-containing small molecules, termed phosphoantigens, and are of interest in the context of the chemotherapy of B cell malignancies. Here, we report the synthesis of four pairs of chiral phosphoantigens: the bromohydrins of isopentenyl diphosphate (Phosphostim(TM)), the epoxides of isopentenyl diphosphate (EIPP); and the corresponding bromohydrin and epoxide analogs of but-3-enyl diphosphate. The ability of each compound to stimulate human Vgamma2Vdelta2 T cells was determined by TNF-alpha release and cell proliferation. In these assays, the (R)-bromohydrin diphosphates were, on average, about twice as active as the (S)-bromohydrin diphosphates. In contrast, the (S)-form of EIPP was about twice as active as (R)-EIPP. The activities of the epoxy but-3-enyl diphosphates were both very low. These results suggest that chiral phosphoantigens, as opposed to racemic mixtures, may have utility in immunotherapy. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.052
• 作为产物：
  描述：

  (R)-dimethyl 2-hydroxy-2-methylsuccinate 在 4-二甲氨基吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Methanesulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-4-methanesulfonyloxy-2-methyl-butyl ester
  参考文献：
  名称：

  Synthesis of chiral phosphoantigens and their activity in γδ T cell stimulation

  摘要：

  gammadelta T cells expressing Vgamma2Vdelta2 T cell receptors are activated by a broad range of phosphorus-containing small molecules, termed phosphoantigens, and are of interest in the context of the chemotherapy of B cell malignancies. Here, we report the synthesis of four pairs of chiral phosphoantigens: the bromohydrins of isopentenyl diphosphate (Phosphostim(TM)), the epoxides of isopentenyl diphosphate (EIPP); and the corresponding bromohydrin and epoxide analogs of but-3-enyl diphosphate. The ability of each compound to stimulate human Vgamma2Vdelta2 T cells was determined by TNF-alpha release and cell proliferation. In these assays, the (R)-bromohydrin diphosphates were, on average, about twice as active as the (S)-bromohydrin diphosphates. In contrast, the (S)-form of EIPP was about twice as active as (R)-EIPP. The activities of the epoxy but-3-enyl diphosphates were both very low. These results suggest that chiral phosphoantigens, as opposed to racemic mixtures, may have utility in immunotherapy. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.052