(S)-ethyl 5-benzyloxy-3,3-ethylendithio-4-<3-(hydroxy)phenyl>pentanoate | 155499-25-5

• 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)-ethyl 5-benzyloxy-3,3-ethylendithio-4-<3-(hydroxy)phenyl>pentanoate
• 英文别名: ethyl 2-[2-[(1S)-1-(3-hydroxyphenyl)-2-phenylmethoxyethyl]-1,3-dithiolan-2-yl]acetate
• CAS: 155499-25-5
• 化学式: C₂₂H₂₆O₄S₂
• 分子量: 418.578
• InChiKey: ORFJVTUQJKNJDT-HXUWFJFHSA-N

物化性质

• 沸点：
  556.3±40.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 5-benzyloxy-3,3-ethylendithio-4-<3-(hydroxy)phenyl>pentanoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以61%的产率得到(4'S)-4'-(phenylmethoxymethyl)spiro[1,3-dithiolane-2,3'-2,4-dihydro-1H-naphthalene]-1',8'-diol
  参考文献：
  名称：

  Chemoenzymatic approach to the AB ring system of aklavinone

  摘要：

  Both enantiomers of compound 3, a possible intermediate for the AB ring system 2 of Aklavinone 1, were obtained in optically active form from diol 7. Key steps were the preparation of both enantiomers of monoacetate 8d, via enzymatic reactions that utilize PPL as catalyst, and the construction of ring A in a totally regioselective manner.

  DOI：

  10.1016/s0040-4039(00)61382-5
• 作为产物：
  描述：

  (S)-ethyl 4-<3-(allyloxy)phenyl>-5-benzyloxy-3-oxopentanoate 在 四(三苯基膦)钯 、 三氟甲磺酸三甲基硅酯 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 4.08h， 生成 (S)-ethyl 5-benzyloxy-3,3-ethylendithio-4-<3-(hydroxy)phenyl>pentanoate
  参考文献：
  名称：

  化学酶促方法与有机金属化学的结合对映体和非对映体选择性合成aklavinone AB环系统

  摘要：

  为了制备标题化合物2，研究了两种不同的方法; 当在化学酶促来源的酯进行了适当的5-烷氧基- （3-羟基苯基）戊酸甲酯的串联还原/分子内羟烷基化，已经承载两个手性中心存在于得到最佳结果2具有正确的相对和绝对立体化学。

  DOI：

  10.1016/0040-4020(96)00804-6

文献信息

• Enantio- and diastereoselective synthesis of the AB ring system of aklavinone by coupling a chemoenzymatic procedure with organometal chemistry
  作者：Luca Banfi、Giuseppe Guanti、Renata Riva

  DOI：10.1016/0040-4020(96)00804-6

  日期：1996.10

  Two different approaches were investigated in order to prepare the title compound 2; best results were obtained when the tandem reduction/intramolecular hydroxyalkylation of the appropriate 5-alkoxy-(3-hydroxyphenyl)pentanoate was performed on an ester of chemoenzymatic origin, already bearing the two chiral centers present in 2 with the correct relative and absolute stereochemistry.

  为了制备标题化合物2，研究了两种不同的方法; 当在化学酶促来源的酯进行了适当的5-烷氧基- （3-羟基苯基）戊酸甲酯的串联还原/分子内羟烷基化，已经承载两个手性中心存在于得到最佳结果2具有正确的相对和绝对立体化学。
• Chemoenzymatic approach to the AB ring system of aklavinone
  作者：Giuseppe Guanti、Luca Banfi、Stefano Brusco、Renata Riva

  DOI：10.1016/s0040-4039(00)61382-5

  日期：1993.1

  Both enantiomers of compound 3, a possible intermediate for the AB ring system 2 of Aklavinone 1, were obtained in optically active form from diol 7. Key steps were the preparation of both enantiomers of monoacetate 8d, via enzymatic reactions that utilize PPL as catalyst, and the construction of ring A in a totally regioselective manner.