3-(trimethylsilylethoxymethoxy)-5-methoxybenzaldehyde | 398142-83-1

• 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: 3-(trimethylsilylethoxymethoxy)-5-methoxybenzaldehyde
• 英文别名: 3-methoxy-5-(2-trimethylsilanylethoxymethoxy)benzaldehyde；3-Methoxy-5-(2-trimethylsilylethoxymethoxy)benzaldehyde
• CAS: 398142-83-1
• 化学式: C₁₄H₂₂O₄Si
• 分子量: 282.412
• InChiKey: VPTFLYTXAWDMCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(trimethylsilylethoxymethoxy)-5-methoxybenzaldehyde 在 4-二甲氨基吡啶 、 正丁基锂 、 甲酸 、 PS-carbodiimide resin 、 四丁基碘化铵 、 potassium carbonate 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 40.0h， 生成 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyric acid [3-(3-carboxypropoxy)-5-methoxyphenyl](2-phenyl[1,3]dithian-2-yl)methyl ester
  参考文献：
  名称：

  Practical Synthesis of a Dithiane-Protected 3‘,5‘-Dialkoxybenzoin Photolabile Safety-Catch Linker for Solid-Phase Organic Synthesis

  摘要：

  The solution-phase preparation of the 3',5'-dialkoxybenzoin photolabile safety-catch linker 16 is described. Pivotal to this convenient synthesis is the selection of appropriate orthogonal protecting groups for the alkoxy functionalities present. The new linker can be readily loaded onto any standard amine-terminating resin under peptide-coupling conditions, without the need to protect the secondary alcohol functionality, and subsequently loaded with substrate. Alternatively, the loading efficiency of sterically hindered substrates can be enhanced by preloading the semiprotected linker variant 10 in solution prior to immobilization onto the resin. This second generation of benzoin photolabile safety-catch linkers provides greater control of both linker loading and resin attachment and should prove to be a more versatile and convenient form of the linker.

  DOI：

  10.1021/jo010703e
• 作为产物：
  描述：

  3-羟基-5-甲氧基苯甲醛 、 2-(三甲基硅烷基)乙氧甲基氯 在 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 以93%的产率得到3-(trimethylsilylethoxymethoxy)-5-methoxybenzaldehyde
  参考文献：
  名称：

  Practical Synthesis of a Dithiane-Protected 3‘,5‘-Dialkoxybenzoin Photolabile Safety-Catch Linker for Solid-Phase Organic Synthesis

  摘要：

  The solution-phase preparation of the 3',5'-dialkoxybenzoin photolabile safety-catch linker 16 is described. Pivotal to this convenient synthesis is the selection of appropriate orthogonal protecting groups for the alkoxy functionalities present. The new linker can be readily loaded onto any standard amine-terminating resin under peptide-coupling conditions, without the need to protect the secondary alcohol functionality, and subsequently loaded with substrate. Alternatively, the loading efficiency of sterically hindered substrates can be enhanced by preloading the semiprotected linker variant 10 in solution prior to immobilization onto the resin. This second generation of benzoin photolabile safety-catch linkers provides greater control of both linker loading and resin attachment and should prove to be a more versatile and convenient form of the linker.

  DOI：

  10.1021/jo010703e

文献信息

• Practical Synthesis of a Dithiane-Protected 3‘,5‘-Dialkoxybenzoin Photolabile Safety-Catch Linker for Solid-Phase Organic Synthesis
  作者：Montserrat Cano、Mark Ladlow、Shankar Balasubramanian

  DOI：10.1021/jo010703e

  日期：2002.1.1

  The solution-phase preparation of the 3',5'-dialkoxybenzoin photolabile safety-catch linker 16 is described. Pivotal to this convenient synthesis is the selection of appropriate orthogonal protecting groups for the alkoxy functionalities present. The new linker can be readily loaded onto any standard amine-terminating resin under peptide-coupling conditions, without the need to protect the secondary alcohol functionality, and subsequently loaded with substrate. Alternatively, the loading efficiency of sterically hindered substrates can be enhanced by preloading the semiprotected linker variant 10 in solution prior to immobilization onto the resin. This second generation of benzoin photolabile safety-catch linkers provides greater control of both linker loading and resin attachment and should prove to be a more versatile and convenient form of the linker.