(3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-6-methylheptanoic acid | 390377-66-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-6-methylheptanoic acid
• 英文别名: (3R,4S)-4-(dibenzylamino)-3-hydroxy-6-methylheptanoic acid
• CAS: 390377-66-9
• 化学式: C₂₂H₂₉NO₃
• 分子量: 355.477
• InChiKey: NEBJOGJHJLTRMV-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-6-methylheptanoic acid 在 palladium dihydroxide 氢气 作用下， 以 溶剂黄146 为溶剂， 80.0 ℃ 、405.3 kPa 条件下， 反应 4.0h， 生成 (3R,4S)-4-amino-3-hydroxy-6-methylheptanoic acid
  参考文献：
  名称：

  Stereoselective synthesis of (3R,4S)-statine utilising the iron acetyl complex [(η5-C5H5)Fe(CO)(PPh3)COMe] as a chiral acetate enolate equivalent.

  摘要：

  Diethylaluminium enolates derived from the iron acetyl complex [(eta5-C5H5)Fe(CO)(PPh3)COMe] undergo highly diastereoselective aldol reactions with the homochiral aldehydes; N,N-dibenzyl valinal and N,N-dibenzyl leucinal. The diastereoselectivity is explained in terms of Masamune's model of double asymmetric indUCtion using the concept of matched and mismatched pairs. The matched pair aldol product arising from the reaction with N,N-dibenzyl leucinal is converted into the known gamma-amino-beta-hydroxy acid, (3R,4S)-statine.

  DOI：

  10.1016/s0040-4020(01)88019-4
• 作为产物：
  描述：

  L-N,N-dibenzylleucine 在 氢氧化钾 、 lithium aluminium tetrahydride 、 正丁基锂 、 溴 、 氯化二乙基铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-6-methylheptanoic acid
  参考文献：
  名称：

  Stereoselective synthesis of (3R,4S)-statine utilising the iron acetyl complex [(η5-C5H5)Fe(CO)(PPh3)COMe] as a chiral acetate enolate equivalent.

  摘要：

  Diethylaluminium enolates derived from the iron acetyl complex [(eta5-C5H5)Fe(CO)(PPh3)COMe] undergo highly diastereoselective aldol reactions with the homochiral aldehydes; N,N-dibenzyl valinal and N,N-dibenzyl leucinal. The diastereoselectivity is explained in terms of Masamune's model of double asymmetric indUCtion using the concept of matched and mismatched pairs. The matched pair aldol product arising from the reaction with N,N-dibenzyl leucinal is converted into the known gamma-amino-beta-hydroxy acid, (3R,4S)-statine.

  DOI：

  10.1016/s0040-4020(01)88019-4

文献信息

• Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes
  作者：José M Andrés、Rafael Pedrosa、Alberto Pérez、Alfonso Pérez-Encabo

  DOI：10.1016/s0040-4020(01)00804-3

  日期：2001.10

  N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-gamma -dibenzylamino-beta -hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding-gamma -amino-beta -hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-gamma -tert-butoxycarbonylamino-beta -hydroxy esters as the major product. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of (3R,4S)-statine utilising the iron acetyl complex [(η5-C5H5)Fe(CO)(PPh3)COMe] as a chiral acetate enolate equivalent.
  作者：Jason W.B. Cooke、Stephen G. Davies、Alan Naylor

  DOI：10.1016/s0040-4020(01)88019-4

  日期：1993.9

  Diethylaluminium enolates derived from the iron acetyl complex [(eta5-C5H5)Fe(CO)(PPh3)COMe] undergo highly diastereoselective aldol reactions with the homochiral aldehydes; N,N-dibenzyl valinal and N,N-dibenzyl leucinal. The diastereoselectivity is explained in terms of Masamune's model of double asymmetric indUCtion using the concept of matched and mismatched pairs. The matched pair aldol product arising from the reaction with N,N-dibenzyl leucinal is converted into the known gamma-amino-beta-hydroxy acid, (3R,4S)-statine.