(4R)-2-(2-carboxyethyl)-4-hydroxymethyl-2-methyloxazolidine-3-carboxylic acid tert-butyl ester | 469886-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-2-(2-carboxyethyl)-4-hydroxymethyl-2-methyloxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: 3-[(4R)-4-(hydroxymethyl)-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-2-yl]propanoic acid
• CAS: 469886-52-0
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: CFDMFUCAUJGWMS-CGCSKFHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-2-(2-carboxyethyl)-4-hydroxymethyl-2-methyloxazolidine-3-carboxylic acid tert-butyl ester 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.25h， 以45.7 mg的产率得到(4S)-2-(2-carboxyethyl)-4-formyl-2-methyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of a Polymer-Supported Oxazolidine Aldehyde for Asymmetric Chemistry

  摘要：

  An expedient synthesis of the polymer-supported aldehyde 3, as a Garner aldehyde equivalent, is described. Oxazolidine 3 may be obtained through preformation of aldehyde linker 4 in solution and loaded onto amine-terminating resin under peptide-coupling conditions, or alternatively via oxidation of polymer-bound alcohol 14. The integrity of the serine-derived stereocenter is maintained through all steps of the synthesis.

  DOI：

  10.1021/jo0203239
• 作为产物：
  描述：

  (4S)-2-(2-benzyloxycarbonylethyl)-4-formyl-2-methyloxazolidine-3-carboxylic acid tert-butyl ester 在 10percent Pd-C sodium tetrahydroborate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 异丙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.75h， 生成 (4R)-2-(2-carboxyethyl)-4-hydroxymethyl-2-methyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of a Polymer-Supported Oxazolidine Aldehyde for Asymmetric Chemistry

  摘要：

  An expedient synthesis of the polymer-supported aldehyde 3, as a Garner aldehyde equivalent, is described. Oxazolidine 3 may be obtained through preformation of aldehyde linker 4 in solution and loaded onto amine-terminating resin under peptide-coupling conditions, or alternatively via oxidation of polymer-bound alcohol 14. The integrity of the serine-derived stereocenter is maintained through all steps of the synthesis.

  DOI：

  10.1021/jo0203239

文献信息

• Synthesis of a Polymer-Supported Oxazolidine Aldehyde for Asymmetric Chemistry
  作者：A. Jonathan Wills、Yamuna Krishnan-Ghosh、Shankar Balasubramanian

  DOI：10.1021/jo0203239

  日期：2002.9.1

  An expedient synthesis of the polymer-supported aldehyde 3, as a Garner aldehyde equivalent, is described. Oxazolidine 3 may be obtained through preformation of aldehyde linker 4 in solution and loaded onto amine-terminating resin under peptide-coupling conditions, or alternatively via oxidation of polymer-bound alcohol 14. The integrity of the serine-derived stereocenter is maintained through all steps of the synthesis.