(2S,5S)-2-(N,N-dibenzylamino)-5-tert-butoxycarbonylamino-1,6-diphenyl-3-hexanone | 162849-97-0

• 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: (2S,5S)-2-(N,N-dibenzylamino)-5-tert-butoxycarbonylamino-1,6-diphenyl-3-hexanone
• 英文别名: tert-butyl N-[(2S,5S)-5-(dibenzylamino)-4-oxo-1,6-diphenylhexan-2-yl]carbamate
• CAS: 162849-97-0
• 化学式: C₃₇H₄₂N₂O₃
• 分子量: 562.752
• InChiKey: PTEZULGTWKGMGW-HEVIKAOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-苯丙氨酸 在 sodium tetrahydroborate 、 potassium carbonate 、 sodium amide 、 溶剂黄146 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲基叔丁基醚 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成 (2S,5S)-2-(N,N-dibenzylamino)-5-tert-butoxycarbonylamino-1,6-diphenyl-3-hexanone
  参考文献：
  名称：

  Reduction of an Enaminone:  Synthesis of the Diamino Alcohol Core of Ritonavir

  摘要：

  The reduction of (SS)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene was optimized for diastereoselectivity and overall conversion to (2S,3S,5S)-5-amino-2-dibenzylamino-3-hydroxy-1,6-diphenylhexane (2a), A two-step reduction sequence is described wherein the enamine is reduced with a borane-sulfonate derivative followed by reduction of the resulting ketone with sodium borohydride. The desired 2a was obtained with 84% diastereoselectivity and an acyclic 1,4 stereoinduction ratio of 14:1, This methodology has been used to produce multikilogram quantities of the diamino alcohol core of Ritonavir and should be general to the synthesis of related diamino hydroxyethylene isosteres.

  DOI：

  10.1021/op9802071

文献信息

• Process for producing optically active diaminohexanone derivative
  申请人：Takasago International Corporation

  公开号：US05523458A1

  公开（公告）日：1996-06-04

  Disclosed herein is a process for producing a (2S,5S)-2,5-diamino-1,6-diphenyl-3-hexanone derivative represented by the formula (1): ##STR1## wherein R.sup.1 means a lower alkylcarbonyl group, a halogen-substituted lower alkylcarbonyl group, an arylcarbonyl group or a lower alkoxycarbonyl group, and R.sup.2 and R.sup.3 are identical with or different from each other and denote individually an aryl group or an alkoxy-substituted aryl group, which comprises subjecting a (2S)-2,5-diamino-1,6-diphenyl-4-hexen-3-one derivative represented by the formula (2): ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the same meaning as defined above, to a hydrogenation reaction in the presence of a transition metal-containing catalyst.

  本发明涉及一种制备式（1）所表示的（2S,5S）-2,5-二氨基-1,6-二苯基-3-己酮衍生物的方法：其中R1表示较低的烷基羰基基团、卤代较低的烷基羰基基团、芳基羰基基团或较低的烷氧羰基基团，而R2和R3相同或不同，分别表示芳基或烷氧基取代的芳基基团。该方法包括将式（2）所表示的（2S）-2,5-二氨基-1,6-二苯基-4-己烯-3-酮衍生物，在过渡金属催化剂的存在下进行氢化反应。其中R1、R2和R3的含义如上所定义。
• US5523458A
  申请人：——

  公开号：US5523458A

  公开（公告）日：1996-06-04
• US5631397A
  申请人：——

  公开号：US5631397A

  公开（公告）日：1997-05-20
• Reduction of an Enaminone:  Synthesis of the Diamino Alcohol Core of Ritonavir
  作者：Anthony R. Haight、Timothy L. Stuk、Michael S. Allen、Lakshmi Bhagavatula、Michael Fitzgerald、Steven M. Hannick、Francis A. J. Kerdesky、Jerome A. Menzia、Shyamal I. Parekh、Timothy A. Robbins、David Scarpetti、Jien-Heh J. Tien

  DOI：10.1021/op9802071

  日期：1999.3.1

  The reduction of (SS)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene was optimized for diastereoselectivity and overall conversion to (2S,3S,5S)-5-amino-2-dibenzylamino-3-hydroxy-1,6-diphenylhexane (2a), A two-step reduction sequence is described wherein the enamine is reduced with a borane-sulfonate derivative followed by reduction of the resulting ketone with sodium borohydride. The desired 2a was obtained with 84% diastereoselectivity and an acyclic 1,4 stereoinduction ratio of 14:1, This methodology has been used to produce multikilogram quantities of the diamino alcohol core of Ritonavir and should be general to the synthesis of related diamino hydroxyethylene isosteres.