L-1,2-O-isopropylidene-5-O-acetyl-3,6-di-O-benzyl-myo-inositol | 1271330-81-4

• 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: L-1,2-O-isopropylidene-5-O-acetyl-3,6-di-O-benzyl-myo-inositol
• 英文别名: (-)-L-5-O-acetyl-3,6-di-O-benzyl-1,2-O-isopropylidene-myo-inositol；[(3aR,4R,5R,6S,7S,7aS)-6-hydroxy-2,2-dimethyl-4,7-bis(phenylmethoxy)-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-5-yl] acetate
• CAS: 1271330-81-4
• 化学式: C₂₅H₃₀O₇
• 分子量: 442.509
• InChiKey: WYFGOFBCPQSUQH-WBCRQVGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  L-1,2-O-isopropylidene-5-O-acetyl-3,6-di-O-benzyl-myo-inositol 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以87%的产率得到1D-5,6-di-O-acetyl-1,4-di-O-benzyl-2,3-O-isopropylidene-myo-inositol
  参考文献：
  名称：

  Kinetic resolution of (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol by lipases: An experimental and theoretical study on the reaction of a key precursor of chiral inositols

  摘要：

  The study on kinetic resolution of two myo-inositol derivatives by lipases is reported. Treatment of the triether derivative, (+/-)-1,2-O-isopropylidene-3,5,6-tri-O-benzyl-myo-inositol, with acylating agents in the presence of different lipases did not afford any detectable amount of acylated products. We speculate that the severe steric hindrance posed by this substrate precluded interaction with the enzymes' catalytic site. Conversely, diol (+/-)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol, a key precursor of chiral myoinositol derivatives, bearing one less benzyl protecting group, underwent a successful transesterification in EtOAc, catalyzed by CaL-B (Novozym 435). Thus, monoacetate L-(-)-1,2-O-isopropylidene-3,6-di-O-benzyl-5-O-acetyl-myo-inositol was regioselectively formed in >99% ee. Additionally, we developed theoretical models of the second tetrahedral intermediate (TI) complex of this reaction to explain the success of the CaL-B and the inactivity of RmL against the same substrate. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.02.001
• 作为产物：
  描述：

  (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 在 吡啶 、 4-二甲氨基吡啶 、 二正丁基氧化锡 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 16.0h， 生成 L-1,2-O-isopropylidene-5-O-acetyl-3,6-di-O-benzyl-myo-inositol
  参考文献：
  名称：

  Efficient kinetic resolution of (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol with the lipase B of Candida antarctica

  摘要：

  (+/−)-1,2-O-异丙叉-3,6-di-O-苄基-myo-肌醇是一种相关的起始材料，在肌醇磷酸及其类似物的合成中具有重要意义。在这项研究中，我们展示了我们朝着利用南极念珠菌（Candida antarctica）B型脂肪酶（Novozym 435）对这种化合物进行高效动力学解析的方法所做的努力。此反应选择性地生成L-(−)-1,2-O-异丙叉-5-O-乙酰基-3,6-di-O-苄基-myo-肌醇。以乙酸乙酯（EtOAc）作为酰化剂时的转化率为34%，而使用醋酸乙烯酯（vinyl acetate）时产率增加至49%以上，同时保持了极高的对映体过量（ee > 99%）。将后者的试剂与TOME作为溶剂相结合，可加速反应。(C) 2010 有限责任公司Elsevier。版权所有。

  DOI：

  10.1016/j.tetasy.2010.12.006

文献信息

• Preparation of core–shell polymer supports to immobilize lipase B from Candida antarctica
  作者：Aline G. Cunha、Marina D. Besteti、Evelin A. Manoel、Angelo A.T. da Silva、Rodrigo V. Almeida、Alessandro B.C. Simas、Roberto Fernandez-Lafuente、José Carlos Pinto、Denise M.G. Freire

  DOI：10.1016/j.molcatb.2013.11.020

  日期：2014.2

  Core-shell supports have been prepared and utilized to immobilize lipase B from Candida antarctica. The hydrophobic nature of the supports permitted to immobilize the enzyme via interfacial activation at low ionic strength. Different supports were prepared having different hydrophobicity and crosslinking degree, and compared to the commercially available. Accurel MP 1000 (hydrophobic macroporous polymer of propylene) is a commercial support described as advantageous in different circumstances and it was used as comparative control in the process of immobilization. The immobilized lipase preparations were evaluated in the hydrolysis of p-nitro-phenyl laurate and the esterification of oleic acid with ethanol. On the kinetic resolution of (+/-)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol, vinyl acetate was used as activated acyl donor. Results were very diverse, as the lipase properties may be easily tuned via immobilization, and some of the supports permitted to obtain activities even a two fold factor higher than the same amount of lipase immobilized in Accurel MP 1000. Moreover, in many instances, the loading of the support with enzyme produced reduced total activity in some reactions while not in other. This was explained by changes in the physical properties of the support surface that may alter the entry of substrates. Supports PS-co-DVB/PS-co-DVB 25% and PMMA-co-DVB/PMMA-co-DVB 25% presented very good features to immobilize CALB. (C) 2013 Elsevier B.V. All rights reserved.