(2S,3R,4E)-2-amino-3-hydroxy-5-thiophen-2-yl-pent-4-enoic acid methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R,4E)-2-amino-3-hydroxy-5-thiophen-2-yl-pent-4-enoic acid methyl ester
• 英文别名: methyl (E,2S,3R)-2-amino-3-hydroxy-5-thiophen-2-ylpent-4-enoate
• 化学式: C₁₀H₁₃NO₃S
• 分子量: 227.284
• InChiKey: AHFWNFIRLLWPDA-VJIGKBMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2E)-3-(2-噻吩基)丙烯醛 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 25.5h， 生成 (2S,3R,4E)-2-amino-3-hydroxy-5-thiophen-2-yl-pent-4-enoic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of δ-heteroaryl substituted β-hydroxy-γ,δ-unsaturated α-amino acids

  摘要：

  Enantiomerically pure 6-heteroaryl substituted beta-hydroxy-gamma, delta-unsaturated alpha-amino acids were stereoselectively synthesized starting from (2R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkoffs reagent) and suitable beta-heteroaryl-alpha, beta-unsaturated aldehydes. The stereocontrolled addition gave a mixture of two diastereoisomers whose configurations were assigned on the basis of spectroscopic data and the accepted model for aldol condensation of the Schollkoffs reagent. Upon controlled hydrolysis the adducts were transformed into the corresponding methyl esters of 6-heteroaryl substituted beta-hydroxy-gamma,delta-unsaturated alpha-amino acids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.023

文献信息

• Stereoselective synthesis of δ-heteroaryl substituted β-hydroxy-γ,δ-unsaturated α-amino acids
  作者：Giuseppe Cremonesi、Piero Dalla Croce、Francesco Fontana、Concetta La Rosa

  DOI：10.1016/j.tetasy.2006.09.023

  日期：2006.10

  Enantiomerically pure 6-heteroaryl substituted beta-hydroxy-gamma, delta-unsaturated alpha-amino acids were stereoselectively synthesized starting from (2R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkoffs reagent) and suitable beta-heteroaryl-alpha, beta-unsaturated aldehydes. The stereocontrolled addition gave a mixture of two diastereoisomers whose configurations were assigned on the basis of spectroscopic data and the accepted model for aldol condensation of the Schollkoffs reagent. Upon controlled hydrolysis the adducts were transformed into the corresponding methyl esters of 6-heteroaryl substituted beta-hydroxy-gamma,delta-unsaturated alpha-amino acids. (c) 2006 Elsevier Ltd. All rights reserved.