[(1R,2S)-2-phenylcyclohexyl] (4S,5R)-3-(4-methylphenyl)sulfonyl-4-(2-methylpropyl)-2-oxo-1,3-oxazolidine-5-carboxylate | 185015-76-3

• 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: [(1R,2S)-2-phenylcyclohexyl] (4S,5R)-3-(4-methylphenyl)sulfonyl-4-(2-methylpropyl)-2-oxo-1,3-oxazolidine-5-carboxylate
• CAS: 185015-76-3
• 化学式: C₂₇H₃₃NO₆S
• 分子量: 499.628
• InChiKey: XFVCTZWKHOPLNC-CXSMSNRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1R,2S)-2-phenylcyclohexyl] (4S,5R)-3-(4-methylphenyl)sulfonyl-4-(2-methylpropyl)-2-oxo-1,3-oxazolidine-5-carboxylate 在 甲醇 、 lithium hydroxide 、 Na-naphthalenide 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 11.0h， 生成 (2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid
  参考文献：
  名称：

  Enantiospecific and diastereoselective synthesis of syn-β-amino-α-hydroxy acids

  摘要：

  The reaction of chiral alpha-hydroxy beta,gamma-unsaturated esters with tosyl isocyanate followed by cyclization of the resulting allylic carbamates with iodine in the presence of sodium carbonate provided trans-4,5-disubstituted 2-oxazolidinone derivatives in a highly diastereoselective manner. The subsequent removal of the iodo group and the protective functionality afforded the syn-beta-amino-alpha-hydroxy acids. Using the reaction sequence, (2R,3S)- and (2S,3R)-3-amino-2-hydroxy acids were synthesized with high enantioselectivity. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00595-8
• 作为产物：
  描述：

  在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以98%的产率得到[(1R,2S)-2-phenylcyclohexyl] (4S,5R)-3-(4-methylphenyl)sulfonyl-4-(2-methylpropyl)-2-oxo-1,3-oxazolidine-5-carboxylate
  参考文献：
  名称：

  Enantiospecific and diastereoselective synthesis of syn-β-amino-α-hydroxy acids

  摘要：

  The reaction of chiral alpha-hydroxy beta,gamma-unsaturated esters with tosyl isocyanate followed by cyclization of the resulting allylic carbamates with iodine in the presence of sodium carbonate provided trans-4,5-disubstituted 2-oxazolidinone derivatives in a highly diastereoselective manner. The subsequent removal of the iodo group and the protective functionality afforded the syn-beta-amino-alpha-hydroxy acids. Using the reaction sequence, (2R,3S)- and (2S,3R)-3-amino-2-hydroxy acids were synthesized with high enantioselectivity. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00595-8

文献信息

• Enantiospecific and diastereoselective synthesis of syn-β-amino-α-hydroxy acids
  作者：Hideyuki Sugimura、Masayuki Miura、Nobuko Yamada

  DOI：10.1016/s0957-4166(97)00595-8

  日期：1997.12

  The reaction of chiral alpha-hydroxy beta,gamma-unsaturated esters with tosyl isocyanate followed by cyclization of the resulting allylic carbamates with iodine in the presence of sodium carbonate provided trans-4,5-disubstituted 2-oxazolidinone derivatives in a highly diastereoselective manner. The subsequent removal of the iodo group and the protective functionality afforded the syn-beta-amino-alpha-hydroxy acids. Using the reaction sequence, (2R,3S)- and (2S,3R)-3-amino-2-hydroxy acids were synthesized with high enantioselectivity. (C) 1997 Elsevier Science Ltd. All rights reserved.