[3-[Dimethyl(phenyl)silyl]oxy-5-hydroxypentyl] acetate | 917387-28-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [3-[Dimethyl(phenyl)silyl]oxy-5-hydroxypentyl] acetate
• 英文别名: [3-[dimethyl(phenyl)silyl]oxy-5-hydroxypentyl] acetate
• CAS: 917387-28-1
• 化学式: C₁₅H₂₄O₄Si
• 分子量: 296.439
• InChiKey: GKJZITGYUVXIOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  [3-[Dimethyl(phenyl)silyl]oxy-5-hydroxypentyl] acetate 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  WO2024062413A1

  摘要：

  公开号：
• 作为产物：
  描述：

  3-羟基戊二酸二甲酯 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 锂硼氢 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 [3-[Dimethyl(phenyl)silyl]oxy-5-hydroxypentyl] acetate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.3109/10242422.2012.661726

文献信息

• 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.
• WO2024062413A1
  申请人：——

  公开号：——

  公开（公告）日：——