(3R,4S,1'R)-2-(α-methylbenzyl)-3-phenyl-4-(phenylsulfenyl)-1,2-thiazetidine 1,1-dioxide | 218460-57-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3R,4S,1'R)-2-(α-methylbenzyl)-3-phenyl-4-(phenylsulfenyl)-1,2-thiazetidine 1,1-dioxide
• 英文别名: (3R,4S)-3-phenyl-2-[(1R)-1-phenylethyl]-4-phenylsulfanylthiazetidine 1,1-dioxide
• CAS: 218460-57-2
• 化学式: C₂₂H₂₁NO₂S₂
• 分子量: 395.546
• InChiKey: WUWSSVRIBBPUNM-YHYVQYDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,1'R)-2-(α-methylbenzyl)-3-phenyl-4-(phenylsulfenyl)-1,2-thiazetidine 1,1-dioxide 在 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (2R,1'R)-S-phenyl 2-(α-methylbenzylamino)phenylthioacetate
  参考文献：
  名称：

  A New Synthesis of α-Amino Acid Thioesters by Pummerer Reaction of 3-Substituted-4-sulfinyl-β-sultams

  摘要：

  alpha-Amino acid thioesters were synthesized by the Pummerer reaction of 3-substituted-4-sulfinyl-beta-sultams with TFAA. The 3-substituted-4-sulfinyl-beta-sultams were prepared from the corresponding beta-sultams by sulfenylation with diphenyl disulfide followed by m-CPBA oxidation. Diastereoselective synthesis of beta-sultams by 1,3-asymmetric induction in [2 + 2] cycloaddition of a sulfene intermediate and chiral imines in solution-phase was studied, and it was found that N-alkylimines gave better diastereoselectivities than N-aralkylimines. The use of imines derived from (R)- and (S)-alpha-methylbenzylamine followed by separation of the major and minor diastereomers gave enantiopure 3-substituted-N-methylbenzyl-beta-sultams. These beta-sultams were then converted to N-methylbenzyl-alpha-amino acid thioesters via sulfenylation and Pummerer rearrangement with high or complete retention of configuration.

  DOI：

  10.1021/jo981230n
• 作为产物：
  描述：

  N-Benzylidene-α-methylbenzylamine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 (3R,4S,1'R)-2-(α-methylbenzyl)-3-phenyl-4-(phenylsulfenyl)-1,2-thiazetidine 1,1-dioxide
  参考文献：
  名称：

  A New Synthesis of α-Amino Acid Thioesters by Pummerer Reaction of 3-Substituted-4-sulfinyl-β-sultams

  摘要：

  alpha-Amino acid thioesters were synthesized by the Pummerer reaction of 3-substituted-4-sulfinyl-beta-sultams with TFAA. The 3-substituted-4-sulfinyl-beta-sultams were prepared from the corresponding beta-sultams by sulfenylation with diphenyl disulfide followed by m-CPBA oxidation. Diastereoselective synthesis of beta-sultams by 1,3-asymmetric induction in [2 + 2] cycloaddition of a sulfene intermediate and chiral imines in solution-phase was studied, and it was found that N-alkylimines gave better diastereoselectivities than N-aralkylimines. The use of imines derived from (R)- and (S)-alpha-methylbenzylamine followed by separation of the major and minor diastereomers gave enantiopure 3-substituted-N-methylbenzyl-beta-sultams. These beta-sultams were then converted to N-methylbenzyl-alpha-amino acid thioesters via sulfenylation and Pummerer rearrangement with high or complete retention of configuration.

  DOI：

  10.1021/jo981230n

文献信息

• A New Synthesis of α-Amino Acid Thioesters by Pummerer Reaction of 3-Substituted-4-sulfinyl-β-sultams
  作者：Tetsuo Iwama、Tadashi Kataoka、Osamu Muraoka、Genzoh Tanabe

  DOI：10.1021/jo981230n

  日期：1998.11.1

  alpha-Amino acid thioesters were synthesized by the Pummerer reaction of 3-substituted-4-sulfinyl-beta-sultams with TFAA. The 3-substituted-4-sulfinyl-beta-sultams were prepared from the corresponding beta-sultams by sulfenylation with diphenyl disulfide followed by m-CPBA oxidation. Diastereoselective synthesis of beta-sultams by 1,3-asymmetric induction in [2 + 2] cycloaddition of a sulfene intermediate and chiral imines in solution-phase was studied, and it was found that N-alkylimines gave better diastereoselectivities than N-aralkylimines. The use of imines derived from (R)- and (S)-alpha-methylbenzylamine followed by separation of the major and minor diastereomers gave enantiopure 3-substituted-N-methylbenzyl-beta-sultams. These beta-sultams were then converted to N-methylbenzyl-alpha-amino acid thioesters via sulfenylation and Pummerer rearrangement with high or complete retention of configuration.