N-Boc-trans-4-tert-butyldimethylsiloxy-L-proline benzyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Boc-trans-4-tert-butyldimethylsiloxy-L-proline benzyl ester
• 英文别名: 2-O-benzyl 1-O-tert-butyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate
• 化学式: C₂₃H₃₇NO₅Si
• 分子量: 435.636
• InChiKey: BFXFQVBYYQVALC-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Boc-trans-4-tert-butyldimethylsiloxy-L-proline benzyl ester 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 barium dihydroxide 、 氢氧化钾 、 重铬酸吡啶 、 次氯酸叔丁酯 、 偶氮二异丁腈 、 dimethyl sulfide borane 、 四丁基氟化铵 、 氢气 、 三正丁基氢锡 、 N,N-二甲基苯胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 生成 (2S,3S,4S)-3-(羧甲基)-4-(2-甲氧基苯基)吡咯烷-2-羧酸
  参考文献：
  名称：

  Synthesis of new acromelic acid congeners: novel neuroexcitatory amino acids acting on glutamate receptor

  摘要：

  A general synthetic method of acromelic acid congeners was developed. Various C4-substituents of this family was introduced by the substitution reaction of the corresponding tosylate with diaryl copper lithium. Phenyl derivative 11 showed comparable excitatory activity with kainic acid, and o-anisyl derivative 12 had most potent activity in this family.

  DOI：

  10.1016/s0040-4039(00)78802-2
• 作为产物：
  描述：

  Boc-L-羟脯氨酸 在 咪唑 、 三乙胺 作用下， 生成 N-Boc-trans-4-tert-butyldimethylsiloxy-L-proline benzyl ester
  参考文献：
  名称：

  Synthesis of new acromelic acid congeners: novel neuroexcitatory amino acids acting on glutamate receptor

  摘要：

  A general synthetic method of acromelic acid congeners was developed. Various C4-substituents of this family was introduced by the substitution reaction of the corresponding tosylate with diaryl copper lithium. Phenyl derivative 11 showed comparable excitatory activity with kainic acid, and o-anisyl derivative 12 had most potent activity in this family.

  DOI：

  10.1016/s0040-4039(00)78802-2

文献信息

• Highly diastereo- and enantioselective direct aldol reactions by 4-tert-butyldimethylsiloxy-substituted organocatalysts derived from N-prolylsulfonamides in water
  作者：Shao-dong Fu、Xiang-kai Fu、Shu-peng Zhang、Xiao-chuan Zou、Xiao-ju Wu

  DOI：10.1016/j.tetasy.2009.09.019

  日期：2009.10

  A new set of 4-tert-butyldimethylsiloxy-substituted organocatalysts derived from N-prolylsulfonamide has been designed and proved to be effective in catalyzing the direct aldol reactions of cyclic ketones with a series of aromatic aldehydes. Furthermore, to the best of our knowledge, there are no reports on the aldol reaction generating the products in very good yields (>99%) and with excellent di

  已设计了一套新的由N-脯氨磺酰胺衍生的4-叔丁基二甲基甲硅烷氧基取代的有机催化剂，并证明可有效催化环酮与一系列芳香醛的直接羟醛反应。此外，据我们所知，尚无关于醛醇缩合反应生成产物的报告，产率很高（> 99％），并且通过使用较低的催化剂具有极佳的非对映选择性（> 99：1）和对映选择性（> 99％）在温和的条件下，在大量水中不添加任何添加剂的情况下（仅3 mol％）进行添加。
• Synthesis of new acromelic acid congeners: novel neuroexcitatory amino acids acting on glutamate receptor
  作者：Kimiko Hashimoto、Haruhisa Shirahama

  DOI：10.1016/s0040-4039(00)78802-2

  日期：1991.6

  A general synthetic method of acromelic acid congeners was developed. Various C4-substituents of this family was introduced by the substitution reaction of the corresponding tosylate with diaryl copper lithium. Phenyl derivative 11 showed comparable excitatory activity with kainic acid, and o-anisyl derivative 12 had most potent activity in this family.