(4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-5-cyclohexylmethyl-2-pyrrolidinone | 335162-38-4

• 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: (4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-5-cyclohexylmethyl-2-pyrrolidinone
• 英文别名: tert-butyl (2R,3S)-2-(cyclohexylmethyl)-5-oxo-3-phenylmethoxypyrrolidine-1-carboxylate
• CAS: 335162-38-4
• 化学式: C₂₃H₃₃NO₄
• 分子量: 387.519
• InChiKey: UCOIQAMYOYHDPU-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-5-cyclohexylmethyl-2-pyrrolidinone 在 palladium on activated charcoal potassium cyanide 、 甲酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 38.0h， 生成 (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：

  (S)-4-benzyloxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione 在 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 31.0h， 生成 (4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-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

• 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
  作者：Bi-Yan He、Tian-Jun Wu、Xian-Yong Yu、Pei-Qiang Huang

  DOI：10.1016/s0957-4166(03)00442-7

  日期：2003.7

  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.