(4S)-2-(2-benzyloxycarbonylethyl)-4-(tert-butyldiphenylsilyloxymethyl)-2-methyloxazolidine-3-carboxylic acid tert-butyl ester | 469886-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S)-2-(2-benzyloxycarbonylethyl)-4-(tert-butyldiphenylsilyloxymethyl)-2-methyloxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-methyl-2-(3-oxo-3-phenylmethoxypropyl)-1,3-oxazolidine-3-carboxylate
• CAS: 469886-49-5
• 化学式: C₃₆H₄₇NO₆Si
• 分子量: 617.858
• InChiKey: WXTMOEMZBBWKDT-FIMWSPJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-2-(2-benzyloxycarbonylethyl)-4-(tert-butyldiphenylsilyloxymethyl)-2-methyloxazolidine-3-carboxylic acid tert-butyl ester 在 10percent Pd-C 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 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
• 作为产物：
  描述：

  氯甲酸苄酯 在 4-二甲氨基吡啶 、 异丙氧基三甲基硅烷 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (4S)-2-(2-benzyloxycarbonylethyl)-4-(tert-butyldiphenylsilyloxymethyl)-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.