tert-butyl N-[(2R,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate

• 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: tert-butyl N-[(2R,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• 化学式: C₃₇H₄₄N₂O₃
• 分子量: 564.768
• InChiKey: FEAVBRDFTRUZPF-PLJDCMBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  61.8
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以92%的产率得到tert-Butyl ((2R,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate
  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
• 作为产物：
  描述：

  N,N-二苄基-L-苯丙氨酸苄酯 在 sodium tetrahydroborate 、 sodium amide 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 甲基叔丁基醚 、 乙腈 为溶剂， 反应 25.5h， 生成 tert-butyl N-[(2R,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate 、 tert-butyl N-[(2R,4R,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate
  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

• 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.