(1S,1'S,2S)-2-<(Boc)amino>-1-(2'-oxocyclopentyl)-3-phenylpropanol | 145473-30-9

• 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: (1S,1'S,2S)-2-<(Boc)amino>-1-(2'-oxocyclopentyl)-3-phenylpropanol
• 英文别名: tert-butyl N-[(1S,2S)-1-hydroxy-1-[(1S)-2-oxocyclopentyl]-3-phenylpropan-2-yl]carbamate
• CAS: 145473-30-9
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: GFLWNMTVVJQGBF-VYDXJSESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氰基磷酸二乙酯 、 (1S,1'S,2S)-2-<(Boc)amino>-1-(2'-oxocyclopentyl)-3-phenylpropanol 在 samarium diiodide 、 锂丁酯 、 叔丁醇 作用下， 生成 (1S,2S,1'R,2'S)-2-<(Boc)amino>-1-(2'-cyanocyclopentyl)-3-phenylpropyl diethyl phosphate
  参考文献：
  名称：

  Synthesis of hydroxyethylene isosteres of the transition state of the HIV protease-catalyzed Phe-Pro hydrolysis: reaction of 2-[(Boc)amino]-1-(2'-oxocyclopentyl)-3-phenylpropanols with diethyl phosphorocyanidate and lithium cyanide followed by samarium iodide

  摘要：

  Reaction of cyclopentanone enolate (7) with BoC-L-Phenylalaninal (6) afforded a mixture of four aldol products 5a-d in a 3:3:1:1 ratio. Reaction of 5a with diethyl phosphorocyanidate followed by samarium iodide reduction afforded lactone 13a and phosphate 12. The structure of 12 was confirmed by X-ray crystallography. Deprotection of 13a gave (1R,1'S,2S,2'S)-2-(2'-amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone (14a), which was transformed to a crystalline lactam 15a under basic conditions. The structure of 15a was also confirmed by X-ray analysis.

  DOI：

  10.1021/jo00069a024
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 、 环戊酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到(1S,1'R,2S)-2-<(Boc)amino>-1-(2'-oxocyclopentyl)-3-phenylpropanol
  参考文献：
  名称：

  Synthesis of hydroxyethylene isosteres of the transition state of the HIV protease-catalyzed Phe-Pro hydrolysis: reaction of 2-[(Boc)amino]-1-(2'-oxocyclopentyl)-3-phenylpropanols with diethyl phosphorocyanidate and lithium cyanide followed by samarium iodide

  摘要：

  Reaction of cyclopentanone enolate (7) with BoC-L-Phenylalaninal (6) afforded a mixture of four aldol products 5a-d in a 3:3:1:1 ratio. Reaction of 5a with diethyl phosphorocyanidate followed by samarium iodide reduction afforded lactone 13a and phosphate 12. The structure of 12 was confirmed by X-ray crystallography. Deprotection of 13a gave (1R,1'S,2S,2'S)-2-(2'-amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone (14a), which was transformed to a crystalline lactam 15a under basic conditions. The structure of 15a was also confirmed by X-ray analysis.

  DOI：

  10.1021/jo00069a024

文献信息

• Synthesis of hydroxyethylene isosteres of the transition state of the HIV protease-catalyzed Phe-Pro hydrolysis: reaction of 2-[(Boc)amino]-1-(2'-oxocyclopentyl)-3-phenylpropanols with diethyl phosphorocyanidate and lithium cyanide followed by samarium iodide
  作者：Marek T. Konieczny、Pascal H. Toma、Mark Cushman

  DOI：10.1021/jo00069a024

  日期：1993.8

  Reaction of cyclopentanone enolate (7) with BoC-L-Phenylalaninal (6) afforded a mixture of four aldol products 5a-d in a 3:3:1:1 ratio. Reaction of 5a with diethyl phosphorocyanidate followed by samarium iodide reduction afforded lactone 13a and phosphate 12. The structure of 12 was confirmed by X-ray crystallography. Deprotection of 13a gave (1R,1'S,2S,2'S)-2-(2'-amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone (14a), which was transformed to a crystalline lactam 15a under basic conditions. The structure of 15a was also confirmed by X-ray analysis.