tert-butyl (4R)-4-(benzylsulfanylmethyl)-5-oxo-1,3-oxazolidine-3-carboxylate | 172096-98-9

• 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: tert-butyl (4R)-4-(benzylsulfanylmethyl)-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 172096-98-9
• 化学式: C₁₆H₂₁NO₄S
• 分子量: 323.413
• InChiKey: BITTXKORDZJICZ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R)-4-(benzylsulfanylmethyl)-5-oxo-1,3-oxazolidine-3-carboxylate 在 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Reaction of ruppert’s reagent (TMS-CF3) with Oxazolidinones: Synthesis of protected α-amino trifluoromethylketones

  摘要：

  (Trifluoromethyl)trimethylsilane adds to alpha-amino acid derived oxazolidin-5-ones in excellent yields. The adducts can be converted into protected alpha-amino trifluoromethylketones by acid hydrolysis.

  DOI：

  10.1016/0040-4039(95)01619-s
• 作为产物：
  描述：

  聚合甲醛 、 Boc-S-苄基-L-半光氨酸 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.0h， 以52%的产率得到tert-butyl (4R)-4-(benzylsulfanylmethyl)-5-oxo-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Reaction of (Trifluoromethyl)trimethylsilane with Oxazolidin-5-ones:  Synthesis of Peptidic and Nonpeptidic Trifluoromethyl Ketones

  摘要：

  (Trifluoromethyl)trimethylsilane (TMS-CF3, the Ruppert Reagent) reacts with a variety of amino acid derived N-substituted oxazolidin-5-ones in excellent yields. Mild acid hydrolysis of adducts with electron-releasing substituents at C-2 affords N-substituted cx-amino trifluoromethyl ketones (TFMKs). N-CBZ-protected alpha-amino TFMKs are converted into hitherto unreported hydrochloride salts of alpha-amino TFMKs by hydrogenolysis. Coupling with aminoacid fluorides gives access to peptidic TFMKs which are of utility as protease inhibitors.

  DOI：

  10.1021/jo980443+

文献信息

• US6043278A
  申请人：——

  公开号：US6043278A

  公开（公告）日：2000-03-28
• Reaction of (Trifluoromethyl)trimethylsilane with Oxazolidin-5-ones:  Synthesis of Peptidic and Nonpeptidic Trifluoromethyl Ketones
  作者：Magnus W. Walter、Robert M. Adlington、Jack E. Baldwin、Christopher J. Schofield

  DOI：10.1021/jo980443+

  日期：1998.7.1

  (Trifluoromethyl)trimethylsilane (TMS-CF3, the Ruppert Reagent) reacts with a variety of amino acid derived N-substituted oxazolidin-5-ones in excellent yields. Mild acid hydrolysis of adducts with electron-releasing substituents at C-2 affords N-substituted cx-amino trifluoromethyl ketones (TFMKs). N-CBZ-protected alpha-amino TFMKs are converted into hitherto unreported hydrochloride salts of alpha-amino TFMKs by hydrogenolysis. Coupling with aminoacid fluorides gives access to peptidic TFMKs which are of utility as protease inhibitors.
• Reaction of ruppert’s reagent (TMS-CF3) with Oxazolidinones: Synthesis of protected α-amino trifluoromethylketones
  作者：Magnus W. Walter、Robert M. Adlington、Jack E. Baldwin、John Chuhan、Christopher J. Schofield

  DOI：10.1016/0040-4039(95)01619-s

  日期：1995.10

  (Trifluoromethyl)trimethylsilane adds to alpha-amino acid derived oxazolidin-5-ones in excellent yields. The adducts can be converted into protected alpha-amino trifluoromethylketones by acid hydrolysis.