tert-butyl (2S,3R,αS)-2-deuterio-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-bromophenyl)propanoate | 1332928-71-8

• 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 (2S,3R,αS)-2-deuterio-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-bromophenyl)propanoate
• 英文别名: tert-butyl (2S,3R)-3-[benzyl-[(1S)-1-phenylethyl]amino]-3-(3-bromophenyl)-2-deuteriopropanoate
• CAS: 1332928-71-8
• 化学式: C₂₈H₃₂BrNO₂
• 分子量: 495.464
• InChiKey: YNAWPUYOYIKWIE-ZXPNDUGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-(3-bromophenyl)acrylic acid tert-butyl ester 、 (S)-(-)-N-苄基-1-苯基-乙胺 在 正丁基锂 、 重水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以72%的产率得到tert-butyl (2S,3R,αS)-2-deuterio-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-bromophenyl)propanoate
  参考文献：
  名称：

  Asymmetric synthesis of syn- and anti-α-deuterio-β3-phenylalanine derivatives

  摘要：

  The conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium beta-amino enolates with D2O provides access to anti configured alpha-deuterio-beta-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (5)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of tert-butyl alpha-deuteriocinnamate esters followed by reaction of the resultant lithium beta-amino enolates with 2-pyridone. After deprotection both the syn- and anti-diastereoisomers of the corresponding alpha-deuterio-beta(3)-amino acids can be isolated in high dr. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.008

文献信息

• Asymmetric synthesis of syn- and anti-α-deuterio-β3-phenylalanine derivatives
  作者：Stephen G. Davies、Emma M. Foster、Catherine R. McIntosh、Paul M. Roberts、Timothy E. Rosser、Andrew D. Smith、James E. Thomson

  DOI：10.1016/j.tetasy.2011.06.008

  日期：2011.5

  The conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium beta-amino enolates with D2O provides access to anti configured alpha-deuterio-beta-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (5)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of tert-butyl alpha-deuteriocinnamate esters followed by reaction of the resultant lithium beta-amino enolates with 2-pyridone. After deprotection both the syn- and anti-diastereoisomers of the corresponding alpha-deuterio-beta(3)-amino acids can be isolated in high dr. (C) 2011 Elsevier Ltd. All rights reserved.