2-acetoxy-3-(4-methoxybenzyloxy)propyl tosylate | 1122090-99-6

• 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: 2-acetoxy-3-(4-methoxybenzyloxy)propyl tosylate
• CAS: 1122090-99-6
• 化学式: C₂₀H₂₄O₇S
• 分子量: 408.472
• InChiKey: RHILDICEIVWVEU-UHFFFAOYSA-N

物化性质

• 沸点：
  550.1±50.0 °C(predicted)
• 密度：
  1.232±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-acetoxy-3-(4-methoxybenzyloxy)propyl tosylate 、 溶剂黄146 在 PS lipase 、 偶氮二甲酸二乙酯 作用下， 以 异丙醚 、 甲苯 为溶剂， 反应 25.0h， 以83%的产率得到(S)-2-acetoxy-3-(4-methoxybenzyloxy)propyl tosylate
  参考文献：
  名称：

  Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine

  摘要：

  The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.005
• 作为产物：
  描述：

  3-(4-甲氧基苄氧基)丙烷-1,2-二醇 、 乙酸酐 、 对甲苯磺酰氯 在 二正丁基氧化锡 、 三乙胺 、 吡啶 、 Porcine Pancreas Lipase 作用下， 以 二氯甲烷 、 异丙醚 为溶剂， 反应 24.0h， 生成 2-acetoxy-3-(4-methoxybenzyloxy)propyl tosylate
  参考文献：
  名称：

  Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine

  摘要：

  The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.005

文献信息

• Preparation of Optically Active 1-<i>O</i>-Alkyl-3-<i>O</i>-arylsulfonyl-<i>sn</i>-glycerol Derivatives: Substrate Engineering in Enzyme-Mediated Enantioselective Hydrolysis
  作者：Kazutsugu Matsumoto、Yasutaka Shimada、Hiroshi Sato、Sachiyo Mochizuki

  DOI：10.1055/s-0028-1083632

  日期：2008.12

  Lipase PS catalyzes the enantioselective hydrolysis of various2-acetyl compounds of the 1- O-alkyl-3- O-arylsulfonyl- SN-glycerolderivatives to afford the corresponding optically active compounds.Changing the structure of the 1- O-alkyland 3- O-arylsulfonyl groups affects boththe reactivity and enantioselectivity. Finally, the E value of the reaction for 2-acetyl-3- O-3,5-dimethylbenzenesulfonyl-1-

  脂肪酶 PS 催化 1-O-烷基-3-O-芳基磺酰基-SN-甘油衍生物的各种 2-乙酰基化合物的对映选择性水解，得到相应的旋光化合物。 改变 1-O-烷基和 3-O- 的结构芳基磺酰基影响反应性和对映选择性。最后，2-乙酰基-3-O-3,5-二甲基苯磺酰基-1-O-4-甲氧基苄基-SN-甘油反应的E值大于200。
• Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine
  作者：Yasutaka Shimada、Kazumasa Usuda、Hirokazu Okabe、Tsuguru Suzuki、Kazutsugu Matsumoto

  DOI：10.1016/j.tetasy.2009.11.005

  日期：2009.12

  The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates. (C) 2009 Elsevier Ltd. All rights reserved.