6-<(tert-butyldimethylsilyl)oxy>-5-hydroxy-3-oxa-5-pivaloylhexanoic acid tert-butyl ester | 217964-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-<(tert-butyldimethylsilyl)oxy>-5-hydroxy-3-oxa-5-pivaloylhexanoic acid tert-butyl ester
• 英文别名: Tert-butyl 2-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-hydroxy-4,4-dimethyl-3-oxopentoxy]acetate
• CAS: 217964-49-3
• 化学式: C₂₀H₄₀O₆Si
• 分子量: 404.62
• InChiKey: MHACNZYQXLEYRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸三甲基硅酯 、 6-<(tert-butyldimethylsilyl)oxy>-5-hydroxy-3-oxa-5-pivaloylhexanoic acid tert-butyl ester 在 2,6-二甲基吡啶 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到6-<(tert-butyldimethylsilyl)oxy>-3-oxa-5-pivaloyl-5-<(trimethylsilyl)oxy>hexanoic acid
  参考文献：
  名称：

  The Pivaloylglycol Anchor Group:  A New Platform for a Photolabile Linker in Solid-Phase Synthesis

  摘要：

  We have designed a new photolabile linker (2) based on 2-pivaloylglycerol for the solid-phase synthesis of acids. The linker was prepared in six steps and anchored to the support via an amide bond. Photocleavage is a two-step process, in which the immobilized acids are released by photolytic generation of a radical center and subsequent spontaneous beta-C,O bond scission. The pivaloyl linker (2) was found to cleave with high yields and purities the acids in various solvents (THF, CH2Cl2, dioxane, DMSO) by irradiation with light above 320 nm. Using this linker, we have demonstrated the solid-phase synthesis of test compounds by peptide synthesis, palladium-catalyzed cross coupling, and epoxidation. The linker proved to be stable toward the treatment with acids and bases. The photolysis rates of our pivaloyl Linker (2) were compared with the rates of a o-nitrobenzyl photolinker (1) and proved to be superior.

  DOI：

  10.1021/jo9816055
• 作为产物：
  描述：

  5-<(tert-butyldimethylsilyl)oxy>-5-cyano-2-methoxy-2-methyl-1,3-dioxane 在 copper(l) iodide 、 potassium carbonate 、 silver(l) oxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 6-<(tert-butyldimethylsilyl)oxy>-5-hydroxy-3-oxa-5-pivaloylhexanoic acid tert-butyl ester
  参考文献：
  名称：

  The Pivaloylglycol Anchor Group:  A New Platform for a Photolabile Linker in Solid-Phase Synthesis

  摘要：

  We have designed a new photolabile linker (2) based on 2-pivaloylglycerol for the solid-phase synthesis of acids. The linker was prepared in six steps and anchored to the support via an amide bond. Photocleavage is a two-step process, in which the immobilized acids are released by photolytic generation of a radical center and subsequent spontaneous beta-C,O bond scission. The pivaloyl linker (2) was found to cleave with high yields and purities the acids in various solvents (THF, CH2Cl2, dioxane, DMSO) by irradiation with light above 320 nm. Using this linker, we have demonstrated the solid-phase synthesis of test compounds by peptide synthesis, palladium-catalyzed cross coupling, and epoxidation. The linker proved to be stable toward the treatment with acids and bases. The photolysis rates of our pivaloyl Linker (2) were compared with the rates of a o-nitrobenzyl photolinker (1) and proved to be superior.

  DOI：

  10.1021/jo9816055

文献信息

• The Pivaloylglycol Anchor Group:  A New Platform for a Photolabile Linker in Solid-Phase Synthesis
  作者：Stefan Peukert、Bernd Giese

  DOI：10.1021/jo9816055

  日期：1998.11.1

  We have designed a new photolabile linker (2) based on 2-pivaloylglycerol for the solid-phase synthesis of acids. The linker was prepared in six steps and anchored to the support via an amide bond. Photocleavage is a two-step process, in which the immobilized acids are released by photolytic generation of a radical center and subsequent spontaneous beta-C,O bond scission. The pivaloyl linker (2) was found to cleave with high yields and purities the acids in various solvents (THF, CH2Cl2, dioxane, DMSO) by irradiation with light above 320 nm. Using this linker, we have demonstrated the solid-phase synthesis of test compounds by peptide synthesis, palladium-catalyzed cross coupling, and epoxidation. The linker proved to be stable toward the treatment with acids and bases. The photolysis rates of our pivaloyl Linker (2) were compared with the rates of a o-nitrobenzyl photolinker (1) and proved to be superior.