dimethyl 3-(dimethylphenylsilyloxy)glutarate | 927403-88-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl 3-(dimethylphenylsilyloxy)glutarate
• 英文别名: Dimethyl 3-(dimethylphenylsilyloxy)glutarate；dimethyl 3-[dimethyl(phenyl)silyl]oxypentanedioate
• CAS: 927403-88-1
• 化学式: C₁₅H₂₂O₅Si
• 分子量: 310.422
• InChiKey: ZZBZDYLYSRJMDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 3-(dimethylphenylsilyloxy)glutarate 在 锂硼氢 、 Zn(N₃)₂*Py₂ 、 偶氮二甲酸二异丙酯 、 Porcine pancreas Chirazyme L-7 lipase 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 68.0h， 生成 (S)-5-azidopentane-1,3-diol
  参考文献：
  名称：

  Lipase catalyzed enantioselective desymmetrization of a prochiral pentane-1,3,5-triol derivative

  摘要：

  The enantioselective desymmetrization of the prochiral 3-O-silyl protected pentanetriol derivative 3 was carefully investigated. At -10 degrees C, the bacterial lipase from Burkholderia cepacia immobilized on ceramic particles led to monoacetate (S)-4 in 52% yield and > 99.9% ee. At a reaction temperature of -40 degrees C the yield and enantioselectivity were even higher, but the reaction time was very long. Theoretical simulations of the reaction progress indicated an enantioselectivity of 25:1 at -10 degrees C and 35:1 at -40 C. (S)-4 was converted into the enantiomerically pure building block 5-azidopentane-1,3-diol (S)-7 in two steps. The absolute configuration of (S)-7 was determined by exciton-coupled circular dichroism (ECCD) of diester (S)-8. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.043
• 作为产物：
  描述：

  3-羟基戊二酸二甲酯 、 苯基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 dimethyl 3-(dimethylphenylsilyloxy)glutarate
  参考文献：
  名称：

  对映体纯的1,3-二恶烷作为高选择性NMDA和σ 1个受体配体

  摘要：

  我们合成并研究了NMDA和σ 1个映体纯的2-（2-苯基-1,3-二恶烷-4-基）的受体亲和力ethanamines 17 - 26。伯胺（[R ，- [R ） - 18 - 20在位置2中的轴向定向的苯基部分高对映选择性（eudismic比70-130）相互作用和高亲和力（ķ我（（[R ，- [R ）- 19）= 13 nM的）和NMDA受体的PCP结合位点。的介绍ñ -苄基部分导致有效的σ 1个配体，包括化合物（小号，R）-22（K i = 6 nM），在位置2具有赤道取向的苯基部分。

  DOI：

  10.1021/jm301166m

文献信息

• Enantiomerically Pure 1,3-Dioxanes as Highly Selective NMDA and σ₁ Receptor Ligands
  作者：Jens Köhler、Klaus Bergander、Jörg Fabian、Dirk Schepmann、Bernhard Wünsch

  DOI：10.1021/jm301166m

  日期：2012.10.25

  We synthesized and investigated the NMDA and σ1 receptor affinity of enantiomerically pure 2-(2-phenyl-1,3-dioxan-4-yl)ethanamines 17–26. The primary amines (R,R)-18–20 with an axially oriented phenyl moiety in position 2 interacted with high enantioselectivity (eudismic ratios 70–130) and high affinity (Ki((R,R)-19) = 13 nM) with the PCP binding site of the NMDA receptor. Introduction of an N-benzyl

  我们合成并研究了NMDA和σ 1个映体纯的2-（2-苯基-1,3-二恶烷-4-基）的受体亲和力ethanamines 17 - 26。伯胺（[R ，- [R ） - 18 - 20在位置2中的轴向定向的苯基部分高对映选择性（eudismic比70-130）相互作用和高亲和力（ķ我（（[R ，- [R ）- 19）= 13 nM的）和NMDA受体的PCP结合位点。的介绍ñ -苄基部分导致有效的σ 1个配体，包括化合物（小号，R）-22（K i = 6 nM），在位置2具有赤道取向的苯基部分。
• Lipase catalyzed enantioselective desymmetrization of a prochiral pentane-1,3,5-triol derivative
  作者：Jens Köhler、Bernhard Wünsch

  DOI：10.1016/j.tetasy.2006.10.043

  日期：2006.11

  The enantioselective desymmetrization of the prochiral 3-O-silyl protected pentanetriol derivative 3 was carefully investigated. At -10 degrees C, the bacterial lipase from Burkholderia cepacia immobilized on ceramic particles led to monoacetate (S)-4 in 52% yield and > 99.9% ee. At a reaction temperature of -40 degrees C the yield and enantioselectivity were even higher, but the reaction time was very long. Theoretical simulations of the reaction progress indicated an enantioselectivity of 25:1 at -10 degrees C and 35:1 at -40 C. (S)-4 was converted into the enantiomerically pure building block 5-azidopentane-1,3-diol (S)-7 in two steps. The absolute configuration of (S)-7 was determined by exciton-coupled circular dichroism (ECCD) of diester (S)-8. (c) 2006 Elsevier Ltd. All rights reserved.
• Conversion of a pentane-1,3,5-triol derivative using lipases as chiral catalysts and possible function of the lid for the regulation of substrate selectivity and enantioselectivity
  作者：Jens Köhler、Bernhard Wünsch

  DOI：10.3109/10242422.2012.661726

  日期：2012.3

  The enantioselective desymmetrization of a prochiral 3-O-silyl protected pentane-1,3,5-triol derivative was achieved by lipase-catalysed hydrolysis. The lipase from B. cepacia led to 95.4% enantiomeric excess (ee) of the (R)-configured compound (R)-4 at a theoretical yield of 79% and was isolated with 98.2% ee and 27% yield. Furthermore, it was found that the ee switched from an excess of (R)-4 to an excess of (S)-4 during the course of the reaction using crude lipase from C. rugosa under the same conditions. This finding was investigated in detail and compared to the change of substrate selectivity known for the lipase from M. miehei. It is supposed that both phenomena may result from a movement of the lid.