(R,S)-2-acetoxy-3-chloropropyl p-toluenesulfonate | 102036-16-8

• 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: (R,S)-2-acetoxy-3-chloropropyl p-toluenesulfonate
• 英文别名: 2-acetoxy-3-chloropropyl tosylate；[1-Chloro-3-(4-methylphenyl)sulfonyloxypropan-2-yl] acetate
• CAS: 102036-16-8
• 化学式: C₁₂H₁₅ClO₅S
• 分子量: 306.767
• InChiKey: PUFMJKGTCYAITN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R,S)-2-acetoxy-3-chloropropyl p-toluenesulfonate 在 脂蛋白脂酶 potassium phosphate buffer 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 (R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Hamaguchi, Shigeki; Ohashi, Takehisa; Watanabe, Kiyoshi, Agricultural and Biological Chemistry, 1986, vol. 50, # 2, p. 375 - 380

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯磺酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (R,S)-2-acetoxy-3-chloropropyl p-toluenesulfonate
  参考文献：
  名称：

  Hamaguchi, Shigeki; Ohashi, Takehisa; Watanabe, Kiyoshi, Agricultural and Biological Chemistry, 1986, vol. 50, # 2, p. 375 - 380

  摘要：

  DOI：

文献信息

• Preparation of Optically Active 1,2-Diol Monotosylates by Enzymatic Hydrolysis
  作者：Kazutsugu Matsumoto、Yasutaka Shimada、Hiroshi Sato、Shinji Minowa

  DOI：10.1055/s-2008-1032047

  日期：2008.2

  An easy preparation of optically active 1,2-diol monotosylate derivatives by enzymatic hydrolysis is disclosed. Lipase PS ( BURKHOLDERIA CEPACIA) catalyzes the hydrolysis of racemic 2-acetoxyhexyl tosylate with excellent enantioselectivity to afford the corresponding optically active compounds. In this reaction, a unique temperature effect is observed. After optimizing the reaction conditions, this

  公开了通过酶促水解容易制备光学活性的1,2-二醇单甲苯磺酸酯衍生物。脂肪酶 PS (BURKHOLDERIA CEPACIA) 以优异的对映选择性催化外消旋甲苯磺酸 2-乙酰氧基己酯的水解，以提供相应的旋光化合物。在该反应中，观察到独特的温度效应。优化反应条件后，该方法可广泛应用于各种高ee光学活性化合物的两种对映体的实际制备。
• Enzymatic method of making 1,2-diol derivatives and their esters with succine anhydride
  申请人：Hwang Ook Soon

  公开号：US20060234362A1

  公开（公告）日：2006-10-19

  The present invention relates to a new process for the preparation of optically active alcohols represented by the general formula 2 and their esters represented by the general formula 3 in scheme 1. In more detail, this invention relates to the process for the preparation of optically active alcohols and their esters which are used as pharmaceutical intermediates by reacting the hydroxyl group stereospecifically by lipase after adding racemic alcohols represented by the general formula 1 and succinic anhydride as an acylating agent to the organic solvent. According to this invention, the primary hydroxyl group of 1,2-diols is transformed by other functional group and the secondary hydroxyl group is esterified stereospecifically with succinic anhydride as an acylating agent. Optically active alcohols and their esters of high optical purity in high yield can be produced by using succinic anhydride as an acylating agent because alcohols can be separated from their esters more easily than those of other conventional methods.

  本发明涉及一种制备光学活性醇的新工艺，其通式为2，以及它们的酯，其通式为3，如图1所示。更详细地说，本发明涉及一种制备光学活性醇及其酯的工艺，通过在有机溶剂中加入通式1的混合醇和琥珀酸酐作为酰化试剂后，通过脂肪酶立体特异性地反应羟基基团。根据本发明，1,2-二醇的主要羟基基团被转化为其他官能团，次要羟基基团通过琥珀酸酐作为酰化试剂被立体特异性地酯化。由于醇可以比其他传统方法更容易地与它们的酯分离，因此可以使用琥珀酸酐作为酰化试剂生产高光学纯度和高收率的光学活性醇及其酯。
• Enzymatic method of making 1,2-diol derivatives and their esters
  申请人：Hwang Ook Soon

  公开号：US20070026508A1

  公开（公告）日：2007-02-01

  The present invention relates to a new process for the preparation of optically active alcohols represented by the general formula 2 and their esters represented by the general formula 3 by enzymatic method from racemic alcohols represented by the general formula 1 in scheme 1. In more details, this invention relates to a process for producing optically active alcohols and their esters which are used as pharmaceutical intermediates from alcohols represented by the general formula 1 by stereospecific transesterification of secondary hydroxyl group using lipases as catalyst with acyl donors in organic solvent or with acyl donors only without using organic solvent. According to this invention, optically active alcohols and esters of high optical purity in high yield can be produced by transforming the primary hydroxyl group of 1,2-diols by tosyl group and transesterifying the secondary hydroxyl group stereospecifically by lipase.

  本发明涉及一种新的方法，通过酶法从通式1所表示的外消旋醇制备通式2所表示的光学活性醇及其酯，通式3。更详细地说，本发明涉及一种从通式1所表示的醇中，使用脂肪酶作为催化剂，通过立体特异性转酯化反应转化次级羟基，使用有机溶剂或仅使用酰基供体而不使用有机溶剂，生产用作制药中间体的光学活性醇及其酯的方法。根据本发明，通过将1,2-二醇的主要羟基转化为对甲苯磺酰基，并通过脂肪酶立体特异性地转酯化次级羟基，可以生产高产率的高光学纯度的光学活性醇和酯。
• Process for preparing optically active glycerol derivates
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0189878A2

  公开（公告）日：1986-08-06

  A process for preparing optically active glycerol derivatives by a biochemical resolution which comprises (i) subjecting an ester having the general formula wherein X is a halogen atom, R is an aliphatic hydrocarbon group of C, to Cs and R' is an aromatic hydrocarbon group or an aliphatic hydrocarbon group of C1 to C2, to the action of enzymes which have a stereo selective esterase activity to asymmetrically hydrolyze the ester to give a mixture of an optically active alcohol and an optically active ester and (ii) obtaining the optically active alcohol and ester by separating operations.

  一种通过生化分解制备光学活性甘油衍生物的工艺，包括(i)将通式为X为卤素原子，R为C至Cs的脂肪族烃基，R'为芳香族烃基或C1至C2的脂肪族烃基的酯，置于具有立体选择性酯酶活性的酶的作用下，使酯不对称水解，得到光学活性醇和光学活性酯的混合物，(ii)通过分离操作得到光学活性醇和酯。
• Immobilization of lipase from Burkholderia cepacia into calcium carbonate microcapsule and its use for enzymatic reactions in organic and aqueous media
  作者：Masahiro Fujiwara、Kumi Shiokawa、Koji Yotsuya、Kazutsugu Matsumoto

  DOI：10.1016/j.molcatb.2014.08.009

  日期：2014.11

  We disclosed a useful procedure for the immobilization of a lipase from Burkholderia cepacia based on its encapsulation into vaterite calcium carbonate microcapsule. The immobilized enzyme had an adequate activity for the hydrolysis of 4-nitrophenyl acetate, which was preserved over 2 years in storage at 4 degrees C. The enantioselective esterification of (+/-)-1-phenylethanol with vinyl acetate using the immobilized lipase smoothly progressed to afford the corresponding optically active compounds, where the enzyme was easily recovered for reuse. Although the hydrolysis of (+/-)-2-acetoxyhexyl tosylate in aqueous solution was catalyzed by the enzyme, the phase transition of calcium carbonate from vaterite to poorly porous calcite during the reaction prevented the access of the reactant to the active site of the lipase, resulting in the significant decrease of the activity of the recovered enzyme. However, the treatment of the immobilized enzyme with zinc chloride solution inhibited the phase transition under the reaction conditions. The enzyme after the zinc treatment was recyclable for the hydrolysis of the substrate without significant decrease of the reactivity even after the uses in aqueous media. (C) 2014 Elsevier B.V. All rights reserved.