tert-butyl (4R)-2,2-dimethyl-4-[(2S)-1-(4-methylphenyl)sulfonylazetidin-2-yl]-1,3-oxazolidine-3-carboxylate | 1178006-06-8

• 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: tert-butyl (4R)-2,2-dimethyl-4-[(2S)-1-(4-methylphenyl)sulfonylazetidin-2-yl]-1,3-oxazolidine-3-carboxylate
• CAS: 1178006-06-8
• 化学式: C₂₀H₃₀N₂O₅S
• 分子量: 410.535
• InChiKey: JPRSNWZTMFRWFI-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R)-2,2-dimethyl-4-[(2S)-1-(4-methylphenyl)sulfonylazetidin-2-yl]-1,3-oxazolidine-3-carboxylate 在 chromium(VI) oxide 、 硫酸 、 水 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以66%的产率得到(2R)-2-[(2S)-1-(4-methylphenyl)sulfonylazetidin-2-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
  参考文献：
  名称：

  Stereoselective synthesis of 2-azetidinylglycine and aminopyrrolidone derivatives from Garner’s aldehyde

  摘要：

  A new route to two hitherto unknown 2-azetidinylglycine derivatives and an aminopyrrolidone derivative has been developed which featured a diastereoselective conjugate addition of benzyl amine to an alpha,beta-unsaturated ester derived from Garner's aldehyde as the key step. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.010
• 作为产物：
  描述：

  tert-butyl (4R)-4-[(1S)-1-amino-3-hydroxypropyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 、 对甲苯磺酰氯 在 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以83%的产率得到tert-butyl (4R)-2,2-dimethyl-4-[(2S)-1-(4-methylphenyl)sulfonylazetidin-2-yl]-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of 2-azetidinylglycine and aminopyrrolidone derivatives from Garner’s aldehyde

  摘要：

  A new route to two hitherto unknown 2-azetidinylglycine derivatives and an aminopyrrolidone derivative has been developed which featured a diastereoselective conjugate addition of benzyl amine to an alpha,beta-unsaturated ester derived from Garner's aldehyde as the key step. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.010

文献信息

• Stereoselective synthesis of 2-azetidinylglycine and aminopyrrolidone derivatives from Garner’s aldehyde
  作者：Latibuddin Thander、Kaushik Sarkar、Shital K. Chattopadhyay

  DOI：10.1016/j.tetasy.2009.04.010

  日期：2009.6

  A new route to two hitherto unknown 2-azetidinylglycine derivatives and an aminopyrrolidone derivative has been developed which featured a diastereoselective conjugate addition of benzyl amine to an alpha,beta-unsaturated ester derived from Garner's aldehyde as the key step. (C) 2009 Elsevier Ltd. All rights reserved.