methylsulfanylmethyl (2S,3R)-3-[bis(2,2,2-trichloroethoxy)phosphoryloxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate | 149203-57-6

• 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: methylsulfanylmethyl (2S,3R)-3-[bis(2,2,2-trichloroethoxy)phosphoryloxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 149203-57-6
• 化学式: C₁₅H₂₄Cl₆NO₈PS
• 分子量: 622.115
• InChiKey: DNLVWJLLWZIYGK-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methylsulfanylmethyl (2S,3R)-3-[bis(2,2,2-trichloroethoxy)phosphoryloxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate 在 magnesium bromide 作用下， 以 乙醚 为溶剂， 生成 (2S,3R)-3-[bis(2,2,2-trichloroethoxy)phosphoryloxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
  参考文献：
  名称：

  A new approach to phosphoserine and phosphothreonine synthons suitable for the stepwise synthesis of phosphopeptides

  摘要：

  Several phosphoserine and phosphothreonine synthons suitable for the stepwise synthesis of phosphopeptides have been prepared. Treatment of methylthiomethyl (MTM) esters of either benzyloxycarbonyl (Z), tert-butyloxycarbonyl (Boc) and allyloxycarbonyl (Alloc) serine and / or threonine with phosphochloridate in pyridine, followed by MgBr2 cleavage of MTM in diethylether, afforded the title compounds in excellent yields.

  DOI：

  10.1016/s0040-4039(00)60441-0
• 作为产物：
  描述：

  Boc-L-苏氨酸 在 吡啶 、 溴代叔丁烷 、 碳酸氢钠 作用下， 反应 12.0h， 生成 methylsulfanylmethyl (2S,3R)-3-[bis(2,2,2-trichloroethoxy)phosphoryloxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
  参考文献：
  名称：

  A new approach to phosphoserine and phosphothreonine synthons suitable for the stepwise synthesis of phosphopeptides

  摘要：

  Several phosphoserine and phosphothreonine synthons suitable for the stepwise synthesis of phosphopeptides have been prepared. Treatment of methylthiomethyl (MTM) esters of either benzyloxycarbonyl (Z), tert-butyloxycarbonyl (Boc) and allyloxycarbonyl (Alloc) serine and / or threonine with phosphochloridate in pyridine, followed by MgBr2 cleavage of MTM in diethylether, afforded the title compounds in excellent yields.

  DOI：

  10.1016/s0040-4039(00)60441-0