(4-methoxyphenyl)methyl (4S,5R)-2-bromo-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-3-oxocyclohexene-1-carboxylate | 202416-40-8

• 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: (4-methoxyphenyl)methyl (4S,5R)-2-bromo-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-3-oxocyclohexene-1-carboxylate
• CAS: 202416-40-8
• 化学式: C₂₁H₂₉BrO₆Si
• 分子量: 485.447
• InChiKey: SQBFNOBPVMVBNV-APWZRJJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  (4-methoxyphenyl)methyl (4S,5R)-2-bromo-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-3-oxocyclohexene-1-carboxylate 在 deuterated potassium phosphate buffer 、 shikimate dehydroge 、 溶剂黄146 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 96.0h， 生成 (3S,4S,5R)-2-bromo-3,4,5-trihydroxycyclohexene-1-carboxylic acid
  参考文献：
  名称：

  Synthesis of 2-Bromo- and 2-Fluoro-3-dehydroshikimic Acids and 2-Bromo- and 2-Fluoroshikimic Acids Using Synthetic and Enzymatic Approaches

  摘要：

  The syntheses of 2-bromo-3-dehydroshikimic acid(1) (5) and 2-bromoshikimic acid(2) (8), are described. Their formation from (2R)-2-bromo-3-dehydroquinic acid (2) using dehydroquinase and shikimate dehydrogenase is also reported. The corresponding enzymatic formation of 2-fluoro-3-dehydroshikimic acid(1) (6) and 2-fluoroshikimic acid(2) (9) from (2R)-2-fluoro-3-dehydroquinic acid (3) are reported.

  DOI：

  10.1021/jo971858i
• 作为产物：
  描述：

  lithium p-methoxybenzyl oxide 在 potassium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (4-methoxyphenyl)methyl (4S,5R)-2-bromo-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-3-oxocyclohexene-1-carboxylate
  参考文献：
  名称：

  Synthesis of 2-Bromo- and 2-Fluoro-3-dehydroshikimic Acids and 2-Bromo- and 2-Fluoroshikimic Acids Using Synthetic and Enzymatic Approaches

  摘要：

  The syntheses of 2-bromo-3-dehydroshikimic acid(1) (5) and 2-bromoshikimic acid(2) (8), are described. Their formation from (2R)-2-bromo-3-dehydroquinic acid (2) using dehydroquinase and shikimate dehydrogenase is also reported. The corresponding enzymatic formation of 2-fluoro-3-dehydroshikimic acid(1) (6) and 2-fluoroshikimic acid(2) (9) from (2R)-2-fluoro-3-dehydroquinic acid (3) are reported.

  DOI：

  10.1021/jo971858i

文献信息

• Synthesis of 2-Bromo- and 2-Fluoro-3-dehydroshikimic Acids and 2-Bromo- and 2-Fluoroshikimic Acids Using Synthetic and Enzymatic Approaches
  作者：C. González-Bello、M. K. Manthey、J. H. Harris、A. R. Hawkins、J. R. Coggins、C. Abell

  DOI：10.1021/jo971858i

  日期：1998.3.1

  The syntheses of 2-bromo-3-dehydroshikimic acid(1) (5) and 2-bromoshikimic acid(2) (8), are described. Their formation from (2R)-2-bromo-3-dehydroquinic acid (2) using dehydroquinase and shikimate dehydrogenase is also reported. The corresponding enzymatic formation of 2-fluoro-3-dehydroshikimic acid(1) (6) and 2-fluoroshikimic acid(2) (9) from (2R)-2-fluoro-3-dehydroquinic acid (3) are reported.