(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsilyloxy)-5-cyanomethylpyrrolidin-2-one | 860302-76-7

• 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: (3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsilyloxy)-5-cyanomethylpyrrolidin-2-one
• 英文别名: tert-butyl (3R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(cyanomethyl)-2-oxopyrrolidine-1-carboxylate
• CAS: 860302-76-7
• 化学式: C₁₇H₃₀N₂O₄Si
• 分子量: 354.522
• InChiKey: OEHFUCBQDUCDSW-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsilyloxy)-5-cyanomethylpyrrolidin-2-one 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、303.98 kPa 条件下， 反应 72.0h， 生成 (3R,5R)-5-(tert-butoxycarbonylamino)-3-(tert-butyldimethylsilyloxy)azepan-2-one
  参考文献：
  名称：

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

  摘要：

  An efficient and stereospecific synthesis of chiral 3,5-diaminoazcpan-2-one as a novel conformationally restricted surrogate of 2.4-diaminobutanoyl (Dab)-Gly dipeptide has been achieved by ail intramolecular transamidation with a catalytic hydrogenation as the key steps, starting from commercially available trans-4-hydroxy-L-proline. This methodology represents a powerful tool for the synthesis of the Dab-Gly dipeptide surrogate as one type of Freidinger epsilon-lactam. epsilon 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.017
• 作为产物：
  描述：

  (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-cyanomethylpyrrolidine 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 10.0h， 以75%的产率得到(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsilyloxy)-5-cyanomethylpyrrolidin-2-one
  参考文献：
  名称：

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

  摘要：

  An efficient and stereospecific synthesis of chiral 3,5-diaminoazcpan-2-one as a novel conformationally restricted surrogate of 2.4-diaminobutanoyl (Dab)-Gly dipeptide has been achieved by ail intramolecular transamidation with a catalytic hydrogenation as the key steps, starting from commercially available trans-4-hydroxy-L-proline. This methodology represents a powerful tool for the synthesis of the Dab-Gly dipeptide surrogate as one type of Freidinger epsilon-lactam. epsilon 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.017

文献信息

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

  DOI：10.1016/j.tetasy.2005.04.017

  日期：2005.6

  An efficient and stereospecific synthesis of chiral 3,5-diaminoazcpan-2-one as a novel conformationally restricted surrogate of 2.4-diaminobutanoyl (Dab)-Gly dipeptide has been achieved by ail intramolecular transamidation with a catalytic hydrogenation as the key steps, starting from commercially available trans-4-hydroxy-L-proline. This methodology represents a powerful tool for the synthesis of the Dab-Gly dipeptide surrogate as one type of Freidinger epsilon-lactam. epsilon 2005 Elsevier Ltd. All rights reserved.