(2S,2'S,2''R,4''S)-2,2'-(1-acetyl-5-oxopropylpyrrolidine-2,4-diyl)-bis(tert-butyldimethylsilanyloxyacetaldehyde) | 874343-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,2'S,2''R,4''S)-2,2'-(1-acetyl-5-oxopropylpyrrolidine-2,4-diyl)-bis(tert-butyldimethylsilanyloxyacetaldehyde)
• 英文别名: (2S)-2-[(3S,5R)-1-acetyl-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy-2-oxoethyl]-2-oxopyrrolidin-3-yl]-2-[tert-butyl(dimethyl)silyl]oxyacetaldehyde
• CAS: 874343-01-8
• 化学式: C₂₂H₄₁NO₆Si₂
• 分子量: 471.742
• InChiKey: KXKFCHALDXSLFM-WJFTUGDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,2'S,2''R,4''S)-2,2'-(1-acetyl-5-oxopropylpyrrolidine-2,4-diyl)-bis(tert-butyldimethylsilanyloxyacetaldehyde) 在 盐酸 、 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 13.0h， 生成 (1S,2S,3R,4R,5S,6R)-6-amino-2,3,4,5-tetrahydroxycycloheptanecarboxylic acid
  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：

  3-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-yl)(trimethylsilanyloxy)methyl]-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 高碘酸 、 三乙胺 、 柠檬酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 生成 (2S,2'S,2''R,4''S)-2,2'-(1-acetyl-5-oxopropylpyrrolidine-2,4-diyl)-bis(tert-butyldimethylsilanyloxyacetaldehyde)
  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

文献信息

• New Enantioselective Entry to Cycloheptane Amino Acid Polyols
  作者：Claudio Curti、Franca Zanardi、Lucia Battistini、Andrea Sartori、Gloria Rassu、Luciana Auzzas、Annamaria Roggio、Luigi Pinna、Giovanni Casiraghi

  DOI：10.1021/jo0520137

  日期：2006.1.1

  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%.