(-)-1-O-acetyl-3-O-benzylpropane-1,2,3-triol | 121787-44-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (-)-1-O-acetyl-3-O-benzylpropane-1,2,3-triol
• 英文别名: [(2R)-2-hydroxy-3-phenylmethoxypropyl] acetate
• CAS: 121787-44-8
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: VVZFZQPMMMTEQX-GFCCVEGCSA-N

物化性质

• 沸点：
  354.8±32.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-1-O-acetyl-3-O-benzylpropane-1,2,3-triol 在 10percent Pd/C 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 4.0h， 生成 (R)-3-acetoxy-2-benzoyloxypropan-1-ol
  参考文献：
  名称：

  嗜热丝状真菌的新型水解酶用于对映体和对映体选择性生物转化

  摘要：

  在两种摇瓶培养基上培养了十四种嗜热丝状真菌，并使用橄榄油，对硝基苯基棕榈酸酯和对硝基苯基丁酸酯作为底物，测定上清液的脂肪酶/羧酸酯酶活性。粗酶粉（丙酮沉淀的上清液）在有机溶剂中作为生物催化剂进行了测试。外消旋1-苯基乙醇（rac - 1）的动力学拆分和2-酰氧基丙烷-1,3-二醇的不对称化（3a，b）通过用乙酸乙烯酯乙酰化选择）以测试这些制剂的生物催化能力。就对映体的选择性而言，经测试的生物催化剂被证明与市售酶相当，而与最常见的市售酶相比，它们表现出更广泛的对位选择性。

  DOI：

  10.1002/adsc.200303027
• 作为产物：
  描述：

  3-苄氧基-1,2-丙二醇 反应 23.0h， 生成 (-)-1-O-acetyl-3-O-benzylpropane-1,2,3-triol
  参考文献：
  名称：

  Regio- and enantioselective esterifications of polyoxygenated compounds catalyzed by lipases

  摘要：

  The lipase catalyzed esterifications of derivatives of propane-1,2,3-triol and butane-1,2,4-triol in organic solvents have been studied. The influence of several factors (lipase source, organic solvent, additives and structural variations in die substrates) on the selectivity have been investigated. Good levels of regio- and enantioselectivity have been achieved, providing practical methods for the synthesis of these chiral building blocks.

  DOI：

  10.1016/s0957-4166(00)80123-8

文献信息

• Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (DAG)
  作者：Giuseppe Guanti、Luca Banfi、Andrea Basso、Elisabetta Bevilacqua、Laura Bondanza、Renata Riva

  DOI：10.1016/j.tetasy.2004.07.040

  日期：2004.9

  A new efficient chemoenzymatic methodology for the production of 3-O-benzyl-sn-glycerol and 1,2-O-dipalmitoyl-sn-glycerol has been developed. It starts from racemic 1-O-benzylglycerol and is based on the sequential enzymatic acylation-Mitsunobu inversion-enzymatic hydrolysis, which has been performed without isolation of the intermediates. In this way a 70-75% yield of 3-O-benzyl-sn-glycerol with 94-96% ee has been obtained. (C) 2004 Published by Elsevier Ltd.
• Baker's yeast mediated reduction of dihydroxyacetone derivatives
  作者：József Bálint、Gabriella Egri、Attila Kolbert、Csilla Dianóczky、Elemér Fogassy、Lajos Novák、László Poppe

  DOI：10.1016/s0957-4166(99)00415-2

  日期：1999.10

  Several monoprotected dihydroxyacetone derivatives 4a-d and their acetates 5a-d were prepared and subjected to biotransformation with baker's yeast. The simple chemical modification of the substrates (i.e. transforming the relatively small hydrophilic hydroxymethyl group into a larger hydrophobic acetoxymethyl moiety) inverted the sense of enantiotope selectivity of these reductions yielding optically active diols 6a-d, or their enantiomeric acetates (7a-d) and diols (ent-6a-d), respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
• ARAGOZZINI, FABRIZIO;MACONI, ELISABETTA;POTENZA, DONATELLA;SCOLASTICO, CA+, SYNTHESIS,(1989) N, C. 225-227
  作者：ARAGOZZINI, FABRIZIO、MACONI, ELISABETTA、POTENZA, DONATELLA、SCOLASTICO, CA+

  DOI：——

  日期：——
• Novel Hydrolases from Thermophilic Filamentous Fungi for Enantiomerically and Enantiotopically Selective Biotransformations
  作者：Viktória Bódai、Réka Peredi、József Bálint、Gabriella Egri、Lajos Novák、György Szakacs、László Poppe

  DOI：10.1002/adsc.200303027

  日期：2003.6

  Fourteen thermophilic filamentous fungi were cultivated on two shake flask media and the supernatants were assayed for lipase/carboxylesterase activities using olive-oil, p-nitrophenyl palmitate and p-nitrophenyl butyrate as substrates. The crude enzyme powders (acetone precipitated supernatants) were tested as biocatalysts in organic solvents. Kinetic resolution of racemic 1-phenylethanol (rac-1)

  在两种摇瓶培养基上培养了十四种嗜热丝状真菌，并使用橄榄油，对硝基苯基棕榈酸酯和对硝基苯基丁酸酯作为底物，测定上清液的脂肪酶/羧酸酯酶活性。粗酶粉（丙酮沉淀的上清液）在有机溶剂中作为生物催化剂进行了测试。外消旋1-苯基乙醇（rac - 1）的动力学拆分和2-酰氧基丙烷-1,3-二醇的不对称化（3a，b）通过用乙酸乙烯酯乙酰化选择）以测试这些制剂的生物催化能力。就对映体的选择性而言，经测试的生物催化剂被证明与市售酶相当，而与最常见的市售酶相比，它们表现出更广泛的对位选择性。
• Regio- and enantioselective esterifications of polyoxygenated compounds catalyzed by lipases
  作者：Bernardo Herradón、Sénida Cueto、Anabel Morcuende、Serafín Valverde

  DOI：10.1016/s0957-4166(00)80123-8

  日期：1993.5

  The lipase catalyzed esterifications of derivatives of propane-1,2,3-triol and butane-1,2,4-triol in organic solvents have been studied. The influence of several factors (lipase source, organic solvent, additives and structural variations in die substrates) on the selectivity have been investigated. Good levels of regio- and enantioselectivity have been achieved, providing practical methods for the synthesis of these chiral building blocks.