Boc-Ser(Me)-Ser(TBDMS)-OEt | 183793-52-4

• 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: Boc-Ser(Me)-Ser(TBDMS)-OEt
• 英文别名: ethyl (2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoate
• CAS: 183793-52-4
• 化学式: C₂₀H₄₀N₂O₇Si
• 分子量: 448.632
• InChiKey: KWRRTRQEFDXOFY-GJZGRUSLSA-N

物化性质

• 沸点：
  520.1±50.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-Ser(Me)-Ser(TBDMS)-OEt 在 劳森试剂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 生成 Boc-thionoSer(Me)-Ser-OEt
  参考文献：
  名称：

  Synthesis of an Enantiomerically Pure Serine-Derived Thiazole

  摘要：

  Previously reported methods for preparing enantiomerically pure thiazoles are inadequate for the synthesis of inherently labile O-alkyl serine-derived thiazoles. The intermediate N-Boc-(O-methylseryl) thiazolines are very susceptible to tautomerization, even under neutral conditions (Scheme 5). Herein, it is demonstrated that the choice of N-protecting group is critical to the preservation of enantiomeric purity. Thus, using an N-trityl protecting group, O-methyl serine was converted to the corresponding N-Boc-(O-methylseryl) thiazole 3 with no appreciable epimerization as indicated by F-19 and H-1 NMR of the corresponding Mosher's amide.

  DOI：

  10.1021/jo961408a
• 作为产物：
  描述：

  保护的甲基-L-丝氨酸二环己基铵盐 在 咪唑 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 Boc-Ser(Me)-Ser(TBDMS)-OEt
  参考文献：
  名称：

  Synthesis of an Enantiomerically Pure Serine-Derived Thiazole

  摘要：

  Previously reported methods for preparing enantiomerically pure thiazoles are inadequate for the synthesis of inherently labile O-alkyl serine-derived thiazoles. The intermediate N-Boc-(O-methylseryl) thiazolines are very susceptible to tautomerization, even under neutral conditions (Scheme 5). Herein, it is demonstrated that the choice of N-protecting group is critical to the preservation of enantiomeric purity. Thus, using an N-trityl protecting group, O-methyl serine was converted to the corresponding N-Boc-(O-methylseryl) thiazole 3 with no appreciable epimerization as indicated by F-19 and H-1 NMR of the corresponding Mosher's amide.

  DOI：

  10.1021/jo961408a

文献信息

• Synthesis of an Enantiomerically Pure Serine-Derived Thiazole
  作者：Jennifer A. Sowinski、Peter L. Toogood

  DOI：10.1021/jo961408a

  日期：1996.1.1

  Previously reported methods for preparing enantiomerically pure thiazoles are inadequate for the synthesis of inherently labile O-alkyl serine-derived thiazoles. The intermediate N-Boc-(O-methylseryl) thiazolines are very susceptible to tautomerization, even under neutral conditions (Scheme 5). Herein, it is demonstrated that the choice of N-protecting group is critical to the preservation of enantiomeric purity. Thus, using an N-trityl protecting group, O-methyl serine was converted to the corresponding N-Boc-(O-methylseryl) thiazole 3 with no appreciable epimerization as indicated by F-19 and H-1 NMR of the corresponding Mosher's amide.