(1'S,1'''S,4''R,4''''R,5R)-3-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-yl)(trimethylsilanyloxy)methyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester | 874342-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (1'S,1'''S,4''R,4''''R,5R)-3-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-yl)(trimethylsilanyloxy)methyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R)-4-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-trimethylsilyloxymethyl]-5-oxo-2H-pyrrole-1-carboxylate
• CAS: 874342-90-2
• 化学式: C₂₄H₄₁NO₉Si
• 分子量: 515.676
• InChiKey: CDJHIVXZCJONSM-QQXKLLMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1'S,1'''S,4''R,4''''R,5R)-3-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-yl)(trimethylsilanyloxy)methyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 2,6-二甲基吡啶 、 ammonium cerium(IV) nitrate 、 氢气 、 sodium acetate 、 柠檬酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 27.0h， 生成 (1^IS,1^IIIS,3S,4^IIR,4^IVR,5R)-3,5-bis[(tert-butyldimethylsilanyloxy)(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-pyrrolidin-2-one
  参考文献：
  名称：

  New Enantioselective Entry to Cycloheptane Amino Acid Polyols

  摘要：

  A diversity-oriented protocol has been developed for the assembly of densely hydroxylated cycloheptane amino acids via succession of a vinylogous Mukaiyama aldol reaction (VMAR), a Morita-Baylis-Hillman reaction (MBHR), and an intramolecular pinacol coupling reaction (IPCR). The plan utilizes Dor L-configured glyceraldehyde derivatives as "chiral" surrogates of glyoxal and N-[(tert-butoxycarbonyl)2-(tert-butyldimethylsilyl)oxy]pyrrole as the synthetic equivalent of the alpha,gamma-dianion of gamma-aminobutanoic acid. The parallel, asymmetric syntheses of four cycloheptane representatives proceed with high diastereocontrol and virtually complete enantioselectivity in ten steps and overall yields of 15-37%.

  DOI：

  10.1021/jo0520137
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 在 吡啶 、 正丁基锂 、 二苯基二硒醚 、 四氯化锡 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (1'S,1'''S,4''R,4''''R,5R)-3-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-yl)(trimethylsilanyloxy)methyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  New Enantioselective Entry to Cycloheptane Amino Acid Polyols

  摘要：

  A diversity-oriented protocol has been developed for the assembly of densely hydroxylated cycloheptane amino acids via succession of a vinylogous Mukaiyama aldol reaction (VMAR), a Morita-Baylis-Hillman reaction (MBHR), and an intramolecular pinacol coupling reaction (IPCR). The plan utilizes Dor L-configured glyceraldehyde derivatives as "chiral" surrogates of glyoxal and N-[(tert-butoxycarbonyl)2-(tert-butyldimethylsilyl)oxy]pyrrole as the synthetic equivalent of the alpha,gamma-dianion of gamma-aminobutanoic acid. The parallel, asymmetric syntheses of four cycloheptane representatives proceed with high diastereocontrol and virtually complete enantioselectivity in ten steps and overall yields of 15-37%.

  DOI：

  10.1021/jo0520137