(S)-2-(N-{(S)-2-(2-furyl)-2-[(2-methoxypropan-2-yl)oxy]ethyl}-4-methylbenzenesulfonamido)-3-phenylpropyl 4-methylbenzenesulfonate | 1225375-86-9

• 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-(2-furyl)-2-[(2-methoxypropan-2-yl)oxy]ethyl}-4-methylbenzenesulfonamido)-3-phenylpropyl 4-methylbenzenesulfonate
• CAS: 1225375-86-9
• 化学式: C₃₃H₃₉NO₈S₂
• 分子量: 641.807
• InChiKey: PILLUEILZGBLNR-IUDBTDONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  44.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112.35
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(N-{(S)-2-(2-furyl)-2-[(2-methoxypropan-2-yl)oxy]ethyl}-4-methylbenzenesulfonamido)-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-(2-furyl)-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
• 作为产物：
  描述：

  (S)-2-({(S)-2-(2-furyl)-2-[(2-methoxypropan-2-yl)oxy]ethyl}amino)-3-phenyl-propan-1-ol 、 对甲苯磺酰氯 在 吡啶 、 三乙胺 、 乙二胺 作用下， 反应 2.5h， 以70%的产率得到(S)-2-(N-{(S)-2-(2-furyl)-2-[(2-methoxypropan-2-yl)oxy]ethyl}-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