(S)-2-{N-[(S)-2-(4-bromophenyl)-2-hydroxyethyl]-4-methylbenzenesulfonamido}-3-phenylpropyl 4-methylbenzenesulfonate | 1225375-93-8

• 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: (S)-2-{N-[(S)-2-(4-bromophenyl)-2-hydroxyethyl]-4-methylbenzenesulfonamido}-3-phenylpropyl 4-methylbenzenesulfonate
• 英文别名: [(2S)-2-[[(2S)-2-(4-bromophenyl)-2-hydroxyethyl]-(4-methylphenyl)sulfonylamino]-3-phenylpropyl] 4-methylbenzenesulfonate
• CAS: 1225375-93-8
• 化学式: C₃₁H₃₂BrNO₆S₂
• 分子量: 658.634
• InChiKey: CUJHYPNOTCFCTQ-QCENPCRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-{N-[(S)-2-(4-bromophenyl)-2-hydroxyethyl]-4-methylbenzenesulfonamido}-3-phenylpropyl 4-methylbenzenesulfonate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以44 mg的产率得到(2S,5S)-5-benzyl-2-(4-bromophenyl)-4-(4-methylbenzenesulfonyl)morpholine
  参考文献：
  名称：

  Enantioselective Chemoenzymatic Synthesis of cis- and trans-2,5-Disubstituted Morpholines

  摘要：

  A versatile synthesis of enantiomerically pure cis- and trans-2,5-disubstituted morpholines is described. Hydroxynitrile lyase-mediated cyanide addition onto aldehydes provided cyanohydrins in virtually quantitative yield and excellent enantioselectivity. Subsequent formation of diastereomerically pure amino esters via a three-step, one-pot reduction-transimination-reduction sequence followed by reduction and simultaneous protection provided cyclization precursors. Finally, cyclization and SmI2-mediated reductive detosylation completed the synthesis of cis- and trans-2,5-disubstituted morpholines in good yields and excellent diastereoselectivities.

  DOI：

  10.1021/jo1003295
• 作为产物：
  描述：

  [(2S)-2-[[(2S)-2-(4-bromophenyl)-2-(2-methoxypropan-2-yloxy)ethyl]-(4-methylphenyl)sulfonylamino]-3-phenylpropyl] 4-methylbenzenesulfonate 在 盐酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 (S)-2-{N-[(S)-2-(4-bromophenyl)-2-hydroxyethyl]-4-methylbenzenesulfonamido}-3-phenylpropyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Enantioselective Chemoenzymatic Synthesis of cis- and trans-2,5-Disubstituted Morpholines

  摘要：

  A versatile synthesis of enantiomerically pure cis- and trans-2,5-disubstituted morpholines is described. Hydroxynitrile lyase-mediated cyanide addition onto aldehydes provided cyanohydrins in virtually quantitative yield and excellent enantioselectivity. Subsequent formation of diastereomerically pure amino esters via a three-step, one-pot reduction-transimination-reduction sequence followed by reduction and simultaneous protection provided cyclization precursors. Finally, cyclization and SmI2-mediated reductive detosylation completed the synthesis of cis- and trans-2,5-disubstituted morpholines in good yields and excellent diastereoselectivities.

  DOI：

  10.1021/jo1003295

文献信息

• Enantioselective Chemoenzymatic Synthesis of <i>cis-</i> and <i>trans</i>-2,5-Disubstituted Morpholines
  作者：Bas Ritzen、Steven Hoekman、Elena Durán Verdasco、Floris L. van Delft、Floris P. J. T. Rutjes

  DOI：10.1021/jo1003295

  日期：2010.5.21

  A versatile synthesis of enantiomerically pure cis- and trans-2,5-disubstituted morpholines is described. Hydroxynitrile lyase-mediated cyanide addition onto aldehydes provided cyanohydrins in virtually quantitative yield and excellent enantioselectivity. Subsequent formation of diastereomerically pure amino esters via a three-step, one-pot reduction-transimination-reduction sequence followed by reduction and simultaneous protection provided cyclization precursors. Finally, cyclization and SmI2-mediated reductive detosylation completed the synthesis of cis- and trans-2,5-disubstituted morpholines in good yields and excellent diastereoselectivities.