(4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone | 607685-51-8

• 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: (4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone
• 英文别名: tert-butyl (2R,3S)-2-(cyclohexylmethyl)-3-hydroxy-5-oxopyrrolidine-1-carboxylate
• CAS: 607685-51-8
• 化学式: C₁₆H₂₇NO₄
• 分子量: 297.395
• InChiKey: AIABJXASZBKTRP-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙醇 、 (4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone 在 potassium cyanide 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以95%的产率得到(3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester
  参考文献：
  名称：

  A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring (2R,3S)-2-aminotetradeca-5,7-dien-3-ol: observation of a remarkable protecting group effect

  摘要：

  A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring antimicrobial (2R,3S)-2-aminotetradeca-5,7-dien-3-ol is reported. The method features a flexible and highly regioselective Grignard addition to (S)-malimide followed by a trans-diastereoselective reductive deoxygenation. The scope and limitations of the highly regio and diastereoselective reductive alkylation of malimides were defined. A remarkable protecting group effect on the regio and diastereoselective reductive alkylation of malimides was observed. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0957-4166(03)00442-7
• 作为产物：
  描述：

  (4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-cyclohexylmethyl-2-pyrrolidinone 在 palladium on activated charcoal 4-二甲氨基吡啶 、 甲酸 、 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 16.0h， 生成 (4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone
  参考文献：
  名称：

  A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring (2R,3S)-2-aminotetradeca-5,7-dien-3-ol: observation of a remarkable protecting group effect

  摘要：

  A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring antimicrobial (2R,3S)-2-aminotetradeca-5,7-dien-3-ol is reported. The method features a flexible and highly regioselective Grignard addition to (S)-malimide followed by a trans-diastereoselective reductive deoxygenation. The scope and limitations of the highly regio and diastereoselective reductive alkylation of malimides were defined. A remarkable protecting group effect on the regio and diastereoselective reductive alkylation of malimides was observed. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0957-4166(03)00442-7

文献信息

• Retroviral protease inhibiting compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0486948A2

  公开（公告）日：1992-05-27

  A retroviral protease inhibiting compound of the formula A -X- B is disclosed. Also disclosed are a composition and method for inhibiting a retroviral protease and for treating an HIV infection. Also disclosed are processes and intermediates useful for the preparation of the retroviral protease inhibitors.

  本发明公开了一种式 A -X- B 的逆转录病毒蛋白酶抑制化合物。还公开了一种抑制逆转录病毒蛋白酶和治疗 HIV 感染的组合物和方法。还公开了用于制备逆转录病毒蛋白酶抑制剂的工艺和中间体。
• Intermediates for preparing retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：EP0997459A1

  公开（公告）日：2000-05-03

  An intermediate of the formula: and an intermediate of the formula: or an acid addition salt thereof.

  公式的中间体： 和 式的中间体 或其酸加成盐。
• US5354866A
  申请人：——

  公开号：US5354866A

  公开（公告）日：1994-10-11
• US5541334A
  申请人：——

  公开号：US5541334A

  公开（公告）日：1996-07-30
• US5554783A
  申请人：——

  公开号：US5554783A

  公开（公告）日：1996-09-10