(1^IR,1^IIIS,3S,4^IIR,4^IVR,5R)-1-acetyl-3,5-bis[(tert-butyldimethylsilanyloxy)(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-pyrrolidin-2-one | 874343-15-4

• 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: (1^IR,1^IIIS,3S,4^IIR,4^IVR,5R)-1-acetyl-3,5-bis[(tert-butyldimethylsilanyloxy)(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-pyrrolidin-2-one
• 英文别名: (3S,5R)-1-acetyl-3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-5-[(S)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]pyrrolidin-2-one
• CAS: 874343-15-4
• 化学式: C₃₀H₅₇NO₈Si₂
• 分子量: 615.955
• InChiKey: VDTVIEYKCULYMC-UDJKJRRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1^IR,1^IIIS,3S,4^IIR,4^IVR,5R)-1-acetyl-3,5-bis[(tert-butyldimethylsilanyloxy)(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-pyrrolidin-2-one 在 盐酸 、 samarium diiodide 、 高碘酸 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 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：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 palladium on activated charcoal 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 二苯基二硒醚 、 氢气 、 sodium acetate 、 四氯化锡 、 三乙胺 、 柠檬酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 35.0h， 生成 (1^IR,1^IIIS,3S,4^IIR,4^IVR,5R)-1-acetyl-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

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%.