(R)-(+)-2-hydroxyhexyl tosylate | 127911-72-2

• 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)-(+)-2-hydroxyhexyl tosylate
• 英文别名: [(2R)-2-hydroxyhexyl] 4-methylbenzenesulfonate
• CAS: 127911-72-2
• 化学式: C₁₃H₂₀O₄S
• 分子量: 272.365
• InChiKey: FXVBWYGCPYKOKG-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-hydroxyhexyl tosylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (R)-(+)-1,2-环氧己烷
  参考文献：
  名称：

  化学酶法获得旋光的1,2-环氧化物

  摘要：

  在有机介质中，脂肪酶催化的酰基转移反应被用于生产旋光性的α-羟基甲苯磺酸酯，该α-羟基甲苯磺酸酯可以容易地转化为具有高光学纯度的相应的1,2-环氧化物。

  DOI：

  10.1016/s0040-4039(01)93924-3
• 作为产物：
  描述：

  Butyric acid 1-(toluene-4-sulfonyloxymethyl)-pentyl ester 在 lipase 、 正丁醇 作用下， 以 正己烷 为溶剂， 反应 120.0h， 生成 (R)-(+)-2-hydroxyhexyl tosylate
  参考文献：
  名称：

  化学酶法获得旋光的1,2-环氧化物

  摘要：

  在有机介质中，脂肪酶催化的酰基转移反应被用于生产旋光性的α-羟基甲苯磺酸酯，该α-羟基甲苯磺酸酯可以容易地转化为具有高光学纯度的相应的1,2-环氧化物。

  DOI：

  10.1016/s0040-4039(01)93924-3

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。
• Process for the enzymatic separation of the optical isomers of tosyloxy-alkanols
  申请人：MINISTERO DELL' UNIVERSITA' E DELLA RICERCA SCIENTIFICA E TECNOLOGICA

  公开号：EP0490407A2

  公开（公告）日：1992-06-17

  Described is a process for the biotechnological resolution, by means of stereoselective enzymatic esterification, of the racemic mixture of optical isomers of tosyloxy-alkanols of general formula (I): wherein R represents an alkyl, haloalkyl or C2-Cio alkenyl group, either linear or branched, and n is 1 or 2, by using aliphatic acid anhydrides in the presence of an enzyme which is capable of selectively catalyzing the esterification of the (R) isomer, leaving the (S) isomer basically unchanged.

  本发明描述了一种通过立体选择性酶法酯化，以生物技术解决通式(I)的对羟基烷 醇光学异构体外消旋混合物的工艺： 其中 R 代表直链或支链烷基、卤代烷基或 C2-Cio 烯基，n 为 1 或 2，使用脂肪族酸酐，在一种酶的存在下，该酶能选择性地催化（R）异构体的酯化反应，而（S）异构体基本不变。
• 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.
• 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.
• CHEN, CHING-SHIH;LIU, YEUK-CHUEN, TETRAHEDRON LETT., 30,(1989) N1, C. 7165-7168
  作者：CHEN, CHING-SHIH、LIU, YEUK-CHUEN

  DOI：——

  日期：——