(1S,1'R,R_S)-[3-dibenzylamino-1-phenyl-2-(toluene-4-sulfinyl)propyl]carbamic acid benzyl ester | 737767-46-3

• 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: (1S,1'R,R_S)-[3-dibenzylamino-1-phenyl-2-(toluene-4-sulfinyl)propyl]carbamic acid benzyl ester
• 英文别名: benzyl N-[(1S,2R)-3-(dibenzylamino)-2-[(R)-(4-methylphenyl)sulfinyl]-1-phenylpropyl]carbamate
• CAS: 737767-46-3
• 化学式: C₃₈H₃₈N₂O₃S
• 分子量: 602.797
• InChiKey: NTWQHNODQKCWHK-ZRQNRMRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,1'R,R_S)-[3-dibenzylamino-1-phenyl-2-(toluene-4-sulfinyl)propyl]carbamic acid benzyl ester 在 2,4,6-三甲基吡啶 、 三氟乙酸酐 作用下， 以 乙腈 为溶剂， 以43%的产率得到(4S,5R)-5-[(Dibenzylamino)-methyl]-4-phenyl-3-p-tolylsulfanyl-oxazolidin-2-one
  参考文献：
  名称：

  Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry

  摘要：

  A novel synthesis of enantiopure hydroxyethylamine isosteres has been developed. Reaction of lithiated beta-sulfinyl-ethylamines 3 with N-Cbz-irnines generated in situ from alpha-amino-sulfones 4 afforded in good to excellent yields and moderate stereocontrol the 2-sulfinyl-1,3-diamines 2. The latter were submitted to the nonoxidative Pummerer reaction (NOPR) in CH2Cl2, that produced the target compounds 1 in very good yields with inversion Of Configuration. In some cases, the use of acetonitrile as solvent resulted in a double-inversion pathway, leading for example to the oxazolidinone 5. The total synthesis of an epimer of Saquinavir has been achieved by this method. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.160
• 作为产物：
  描述：

  benzyl phenyl(phenylsulfonyl)methylcarbamate 、 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (1R,1'S,R_S)-[3-dibenzylamino-1-phenyl-2-(toluene-4-sulfinyl)propyl]carbamic acid benzyl ester 、 (1S,1'S,R_S)-[3-dibenzylamino-1-phenyl-2-(toluene-4-sulfinyl)propyl]carbamic acid benzyl ester 、 (1R,1'R,R_S)-[3-dibenzylamino-1-phenyl-2-(toluene-4-sulfinyl)propyl]carbamic acid benzyl ester 、 (1S,1'R,R_S)-[3-dibenzylamino-1-phenyl-2-(toluene-4-sulfinyl)propyl]carbamic acid benzyl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry

  摘要：

  A novel synthesis of enantiopure hydroxyethylamine isosteres has been developed. Reaction of lithiated beta-sulfinyl-ethylamines 3 with N-Cbz-irnines generated in situ from alpha-amino-sulfones 4 afforded in good to excellent yields and moderate stereocontrol the 2-sulfinyl-1,3-diamines 2. The latter were submitted to the nonoxidative Pummerer reaction (NOPR) in CH2Cl2, that produced the target compounds 1 in very good yields with inversion Of Configuration. In some cases, the use of acetonitrile as solvent resulted in a double-inversion pathway, leading for example to the oxazolidinone 5. The total synthesis of an epimer of Saquinavir has been achieved by this method. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.160

文献信息

• Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry
  作者：Cristina Pesenti、Alberto Arnone、Paolo Arosio、Massimo Frigerio、Stefano V. Meille、Walter Panzeri、Fiorenza Viani、Matteo Zanda

  DOI：10.1016/j.tetlet.2004.04.160

  日期：2004.6

  A novel synthesis of enantiopure hydroxyethylamine isosteres has been developed. Reaction of lithiated beta-sulfinyl-ethylamines 3 with N-Cbz-irnines generated in situ from alpha-amino-sulfones 4 afforded in good to excellent yields and moderate stereocontrol the 2-sulfinyl-1,3-diamines 2. The latter were submitted to the nonoxidative Pummerer reaction (NOPR) in CH2Cl2, that produced the target compounds 1 in very good yields with inversion Of Configuration. In some cases, the use of acetonitrile as solvent resulted in a double-inversion pathway, leading for example to the oxazolidinone 5. The total synthesis of an epimer of Saquinavir has been achieved by this method. (C) 2004 Elsevier Ltd. All rights reserved.