(4S,5R)-4-Cyclohexylmethyl-2-oxo-3-(toluene-4-sulfonyl)-oxazolidine-5-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester | 185015-74-1

• 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: (4S,5R)-4-Cyclohexylmethyl-2-oxo-3-(toluene-4-sulfonyl)-oxazolidine-5-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester
• CAS: 185015-74-1
• 化学式: C₃₀H₃₇NO₆S
• 分子量: 539.693
• InChiKey: LLHCTHAHCFNAPA-YVHASNINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  89.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-Cyclohexylmethyl-2-oxo-3-(toluene-4-sulfonyl)-oxazolidine-5-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester 在 甲醇 、 lithium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.0h， 生成 (2R,3S)-4-Cyclohexyl-2-hydroxy-3-(toluene-4-sulfonylamino)-butyric 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：

  (R)-4-(Cyclohexyl-iodo-methyl)-2-oxo-3-(toluene-4-sulfonyl)-oxazolidine-5-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester 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(4S,5R)-4-Cyclohexylmethyl-2-oxo-3-(toluene-4-sulfonyl)-oxazolidine-5-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester
  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