2-methylpropyl (2S,4R)-4-benzyl-4-methyl-5-oxo-2-(4-phenylphenyl)-1,3-oxazolidine-3-carboxylate | 346578-00-5

• 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: 2-methylpropyl (2S,4R)-4-benzyl-4-methyl-5-oxo-2-(4-phenylphenyl)-1,3-oxazolidine-3-carboxylate
• CAS: 346578-00-5
• 化学式: C₂₈H₂₉NO₄
• 分子量: 443.543
• InChiKey: BVMLWFBUHFWCAA-LBNVMWSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methylpropyl (2S,4R)-4-benzyl-4-methyl-5-oxo-2-(4-phenylphenyl)-1,3-oxazolidine-3-carboxylate 在 盐酸 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 生成 (R)-α-methyl-phenylalanine hydrochloride
  参考文献：
  名称：

  Crystallization-induced asymmetric transformations and self-regeneration of stereocenters (SROSC): enantiospecific synthesis of α-benzylalanine and hydantoin BIRT-377

  摘要：

  N-lsobutoxycarbonyl protected L-alanine was condensed with 4-phenylbenzaldehyde in a crystallization-controlled process to give the corresponding c is-oxazolidinone derivative as the sole product in high yield this underwent enolization and benzylation with the typical high degree of stereoselectivity observed in the SROSC involving this class of compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00403-8
• 作为产物：
  描述：

  N-isobutyloxycarbonyl-(S)-alanine 在 草酰氯 、 四氯化锡 、 N,N-二甲基甲酰胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 2-methylpropyl (2S,4R)-4-benzyl-4-methyl-5-oxo-2-(4-phenylphenyl)-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  The Formation of a Crystalline Oxazolidin-5-one from (L)-Alanine and its Use as a Chiral Template in the Practical Synthesis of α-Substituted Alanine Esters

  摘要：

  研究了三种不同的合成噁唑烷-5-酮的方法，旨在开发一种合成对映异构体纯度高的噁唑烷-5-酮的方法。报道了一种新颖的方法，利用动态结晶诱导的不对称转化，在千克级别上以92%的产率分离出一种噁唑烷-5-酮的单一对映异构体。噁唑烷-5-酮模板的烷基化可导致N-保护的α-取代丙氨酸酯以>98–99% ee的良好至优异产率。

  DOI：

  10.2533/chimia.2006.566

文献信息

• Crystallization-induced asymmetric transformations and self-regeneration of stereocenters (SROSC): enantiospecific synthesis of α-benzylalanine and hydantoin BIRT-377
  作者：Elio Napolitano、Vittorio Farina

  DOI：10.1016/s0040-4039(01)00403-8

  日期：2001.4

  N-lsobutoxycarbonyl protected L-alanine was condensed with 4-phenylbenzaldehyde in a crystallization-controlled process to give the corresponding c is-oxazolidinone derivative as the sole product in high yield this underwent enolization and benzylation with the typical high degree of stereoselectivity observed in the SROSC involving this class of compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.
• The Formation of a Crystalline Oxazolidin-5-one from (L)-Alanine and its Use as a Chiral Template in the Practical Synthesis of α-Substituted Alanine Esters
  作者：Eriksson, Magnus、Napolitano, Elio、Xu, Jinghua、Kapadia, Suresh、Byrne, Denis、Nummy, Laurence、Grinberg, Nelu、Shen, Sherri、Lee, Heewon、Farina, Vittorio

  DOI：10.2533/chimia.2006.566

  日期：——

  Three different protocols to synthesize oxazolidin-5-ones have been studied with the goal to develop a method to synthesize a diastereomerically pure oxazolidin-5-one. A novel method is reported that uses a dynamic crystallization-induced asymmetric transformation to isolate a single diastereomer of an oxazolidin-5-one in 92% yield on kilogram scale. Alkylation of the oxazolidin-5-one template leads to good-to-excellent yields of N-protected α-substituted alanine esters in >98–99% ee.

  研究了三种不同的合成噁唑烷-5-酮的方法，旨在开发一种合成对映异构体纯度高的噁唑烷-5-酮的方法。报道了一种新颖的方法，利用动态结晶诱导的不对称转化，在千克级别上以92%的产率分离出一种噁唑烷-5-酮的单一对映异构体。噁唑烷-5-酮模板的烷基化可导致N-保护的α-取代丙氨酸酯以>98–99% ee的良好至优异产率。