benzyl (4S)-4-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate | 352636-79-4

• 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: benzyl (4S)-4-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 352636-79-4
• 化学式: C₁₉H₂₉NO₅Si
• 分子量: 379.528
• InChiKey: IJCAJRVHZINTBK-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (4S)-4-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate 在 三乙基硅烷 作用下， 以 氯仿 、 三氟乙酸 为溶剂， 以92%的产率得到Cbz-N-MeThr(TBS)-OH
  参考文献：
  名称：

  Synthesis of N-protected N-methyl serine and threonine

  摘要：

  Two efficient and convenient synthesis of N-Cbz and N-Fmoc N-methyl serine and threonine an described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00606-2
• 作为产物：
  描述：

  N-苄氧羰基-L-苏氨酸 在 咪唑 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 49.0h， 生成 benzyl (4S)-4-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxo-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of N-protected N-methyl serine and threonine

  摘要：

  Two efficient and convenient synthesis of N-Cbz and N-Fmoc N-methyl serine and threonine an described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00606-2

文献信息

• Synthesis of N-protected N-methyl serine and threonine
  作者：Yue Luo、Ghotas Evindar、Dan Fishlock、Gilles A Lajoie

  DOI：10.1016/s0040-4039(01)00606-2

  日期：2001.6

  Two efficient and convenient synthesis of N-Cbz and N-Fmoc N-methyl serine and threonine an described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone. (C) 2001 Published by Elsevier Science Ltd.