(2R,4S,5S)-5-Dibenzylamino-4-hydroxy-6-phenyl-2-propyl-hexanoic acid methyl ester | 194551-80-9

• 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: (2R,4S,5S)-5-Dibenzylamino-4-hydroxy-6-phenyl-2-propyl-hexanoic acid methyl ester
• 英文别名: methyl (2R,4S,5S)-5-(dibenzylamino)-4-hydroxy-6-phenyl-2-propylhexanoate
• CAS: 194551-80-9
• 化学式: C₃₀H₃₇NO₃
• 分子量: 459.629
• InChiKey: PEUUFXSHGIZNST-ULNSLHSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (2R,4S,5S)-5-Dibenzylamino-4-hydroxy-6-phenyl-2-propyl-hexanoic acid methyl ester 在 palladium on activated charcoal 1,4-环己二烯 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以67%的产率得到(2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-propyl-hexanoic acid methyl ester
  参考文献：
  名称：

  A Stereocontrolled, Convergent Synthesis of Hydroxyethylene Dipeptide Isosteres

  摘要：

  A simple, convergent, and stereoselective synthesis of hydroxyethylene dipeptide isosteres 1 and 2 from scalemic alpha-hydroxy esters has been developed. The method is short (six steps), efficient (approximate to 15-25% overall), and highly diastereoselective (86-94% de) and enantioselective (> 95% ee).

  DOI：

  10.1021/jo970579s
• 作为产物：
  描述：

  tert-butyl 4-(N,N-dibenzylamino)-3-oxo-5-phenylpentanoate 在 sodium tetrahydroborate 、 sodium hydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 52.17h， 生成 (2R,4S,5S)-5-Dibenzylamino-4-hydroxy-6-phenyl-2-propyl-hexanoic acid methyl ester
  参考文献：
  名称：

  A Stereocontrolled, Convergent Synthesis of Hydroxyethylene Dipeptide Isosteres

  摘要：

  A simple, convergent, and stereoselective synthesis of hydroxyethylene dipeptide isosteres 1 and 2 from scalemic alpha-hydroxy esters has been developed. The method is short (six steps), efficient (approximate to 15-25% overall), and highly diastereoselective (86-94% de) and enantioselective (> 95% ee).

  DOI：

  10.1021/jo970579s

文献信息

• A Stereocontrolled, Convergent Synthesis of Hydroxyethylene Dipeptide Isosteres
  作者：Junhua Tao、Robert V. Hoffman

  DOI：10.1021/jo970579s

  日期：1997.9.1

  A simple, convergent, and stereoselective synthesis of hydroxyethylene dipeptide isosteres 1 and 2 from scalemic alpha-hydroxy esters has been developed. The method is short (six steps), efficient (approximate to 15-25% overall), and highly diastereoselective (86-94% de) and enantioselective (> 95% ee).