(3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one | 849624-40-4

• 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: (3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one
• 英文别名: (3R,5S)-5-(azidomethyl)-3-[tert-butyl(dimethyl)silyl]oxy-1-(4-methylphenyl)sulfonylpyrrolidin-2-one
• CAS: 849624-40-4
• 化学式: C₁₈H₂₈N₄O₄SSi
• 分子量: 424.596
• InChiKey: AQUXZWXSZHUQFY-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、303.97 kPa 条件下， 反应 48.0h， 以80%的产率得到(3R,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-toluenesulfonylamino)-piperidin-2-one
  参考文献：
  名称：

  Synthesis of (3S,5S)-3,5-diaminopiperidin-2-one as a conformationally restricted surrogate of Dab-Gly dipeptide

  摘要：

  An efficient and stereospecific synthesis of chiral 3,5-diaminopiperidin-2-one as a novel conformationally restricted surrogate of 2,4-diaminobutanoyl (Dab)-Gly dipeptide has been achieved. The key steps include (i) ruthenium tetroxide (RuO4) oxidation of N-Boc-2-azidometliylpyrrolidines with a catalytic amount of RuO2.xH(2)O in a two-phase system of aq NaIO4/AcOEt and (ii) intramolecular transamidation of the resulting 2-azidomethylpyrrolidin-2-ones with 10% Pd-C in MeOH/H2O (12/1, v/v) under an H-2 atmosphere (3 atm). This methodology represents a powerful tool for the synthesis of Dab-Gly dipeptide surrogate. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.018
• 作为产物：
  描述：

  (2S,4R)-2-(azidomethyl)-1-(tert-butoxycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine 在 4-二甲氨基吡啶 、 ruthenium(IV) oxide 、 sodium periodate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 16.0h， 生成 (3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of (3S,5S)-3,5-diaminopiperidin-2-one as a conformationally restricted surrogate of Dab-Gly dipeptide

  摘要：

  An efficient and stereospecific synthesis of chiral 3,5-diaminopiperidin-2-one as a novel conformationally restricted surrogate of 2,4-diaminobutanoyl (Dab)-Gly dipeptide has been achieved. The key steps include (i) ruthenium tetroxide (RuO4) oxidation of N-Boc-2-azidometliylpyrrolidines with a catalytic amount of RuO2.xH(2)O in a two-phase system of aq NaIO4/AcOEt and (ii) intramolecular transamidation of the resulting 2-azidomethylpyrrolidin-2-ones with 10% Pd-C in MeOH/H2O (12/1, v/v) under an H-2 atmosphere (3 atm). This methodology represents a powerful tool for the synthesis of Dab-Gly dipeptide surrogate. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.018

文献信息

• Synthesis of (3S,5S)-3,5-diaminopiperidin-2-one as a conformationally restricted surrogate of Dab-Gly dipeptide
  作者：Ken-ichi Tanaka、Harumitsu Nemoto、Hiroyuki Sawanishi

  DOI：10.1016/j.tetasy.2004.12.018

  日期：2005.2

  An efficient and stereospecific synthesis of chiral 3,5-diaminopiperidin-2-one as a novel conformationally restricted surrogate of 2,4-diaminobutanoyl (Dab)-Gly dipeptide has been achieved. The key steps include (i) ruthenium tetroxide (RuO4) oxidation of N-Boc-2-azidometliylpyrrolidines with a catalytic amount of RuO2.xH(2)O in a two-phase system of aq NaIO4/AcOEt and (ii) intramolecular transamidation of the resulting 2-azidomethylpyrrolidin-2-ones with 10% Pd-C in MeOH/H2O (12/1, v/v) under an H-2 atmosphere (3 atm). This methodology represents a powerful tool for the synthesis of Dab-Gly dipeptide surrogate. (C) 2005 Elsevier Ltd. All rights reserved.