(2S,3S)-2-azido-3-(2-cyclopropylacetoxy)-3-phenylpropionic 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,3S)-2-azido-3-(2-cyclopropylacetoxy)-3-phenylpropionic acid methyl ester
• 英文别名: methyl (2S,3S)-2-azido-3-(2-cyclopropylacetyl)oxy-3-phenylpropanoate
• 化学式: C₁₅H₁₇N₃O₄
• 分子量: 303.318
• InChiKey: QTDWTYRXRBUPEQ-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-azido-3-(2-cyclopropylacetoxy)-3-phenylpropionic acid methyl ester 在 tin(II) chloride dihdyrate 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 以73%的产率得到(2S,3S)-2-(2-cyclopropylacetylamino)-3-hydroxy-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of 2,4,5-Trisubstituted Δ²-Thiazolines

  摘要：

  AbstractΔ2‐Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5‐trisubstituted Δ2‐thiazolines. These Δ2‐thiazolines were synthesized from readily accessible/commercially available α,β‐unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O→N acyl migration reaction as key steps. The final products were obtained in good yields with up to 97 % enantiomeric excess.

  DOI：

  10.1002/chem.201301120
• 作为产物：
  描述：

  甲基 (2R,3S)-(+)-2,3-二羟基-3-苯基丙酸盐 在 4-二甲氨基吡啶 、 sodium azide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 (2S,3S)-2-azido-3-(2-cyclopropylacetoxy)-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of 2,4,5-Trisubstituted Δ²-Thiazolines

  摘要：

  AbstractΔ2‐Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5‐trisubstituted Δ2‐thiazolines. These Δ2‐thiazolines were synthesized from readily accessible/commercially available α,β‐unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O→N acyl migration reaction as key steps. The final products were obtained in good yields with up to 97 % enantiomeric excess.

  DOI：

  10.1002/chem.201301120

文献信息

• Asymmetric Synthesis of 2,4,5-Trisubstituted Δ²-Thiazolines
  作者：Christoffer Bengtsson、Hanna Nelander、Fredrik Almqvist

  DOI：10.1002/chem.201301120

  日期：2013.7.22

  AbstractΔ2‐Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5‐trisubstituted Δ2‐thiazolines. These Δ2‐thiazolines were synthesized from readily accessible/commercially available α,β‐unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O→N acyl migration reaction as key steps. The final products were obtained in good yields with up to 97 % enantiomeric excess.