(S)-2-Benzyloxycarbonylamino-succinic acid bis-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl) ester | 194492-66-5

• 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: (S)-2-Benzyloxycarbonylamino-succinic acid bis-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl) ester
• CAS: 194492-66-5
• 化学式: C₂₄H₃₃NO₁₀
• 分子量: 495.527
• InChiKey: PIELRDGOMZAAMM-ACBHZAAOSA-N

物化性质

• 沸点：
  624.0±55.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  127.85
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxycarbonylamino-succinic acid bis-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl) ester 在 palladium/alumina 盐酸 、 Novozyme 、 3-戊酮 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 41.0h， 生成
  参考文献：
  名称：

  化学酶促合成氨基酸基表面活性剂

  摘要：

  AbstractThe application of lipases to the synthesis of amino acid‐based surfactants was investigated. Low yields (2–9%) were obtained in the acylation of free amino acids, such as l‐serine and l‐lysine, as well as their ethyl esters and amides with fatty acids, owing in part to low miscibility of the reactants. When the N‐carbobenzyloxy (Cbz)‐l‐amino acids were used in an effort to improve miscibility of the amino acid derivatives with the acyl donor, a dramatic improvement was observed for N‐Cbz‐l‐serine (92% yield) but not for Nα‐Cbz‐ or Nζ‐Cbz‐l‐lysine (7 and 2% yield, respectively). As an alternative, and efficient synthesis of Nζ‐acyl‐l‐lysines was developed, based on the regiospecific chemical acylation of copper(II) lysinate. In pursuit of a general route to amino acid‐fatty acid surfactants, the utility of a polyol linker was investigated. Thus, the glycerol ester of Nα′Nζ‐di‐Cbz‐l‐lysine was prepared and evaluated as a substrate for acylation. As expected, this and other glycer‐1‐yl esters of N‐protected amino acids were excellent substrates for lipase‐catalyzed acylation. Their reaction with myristic acid in the presence of Novozyme resulted in the regioselective acylation of the primary hydroxyl group of the glycerol moiety to afford the corresponding 1‐O‐(N‐Cbz‐l‐aminoacyl)‐3‐O‐myris‐toylglycerols with conversions of 50–90%. These were readily deprotected to give a range of 1‐O‐(aminoacyl)‐3‐O‐myristoyl‐glycerols with overall yields of 27–71%.

  DOI：

  10.1007/s11746-997-0232-8
• 作为产物：
  描述：

  N-CBZ-L-天冬氨酸 、 丙酮缩甘油 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以70%的产率得到(S)-2-Benzyloxycarbonylamino-succinic acid bis-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl) ester
  参考文献：
  名称：

  化学酶促合成氨基酸基表面活性剂

  摘要：

  AbstractThe application of lipases to the synthesis of amino acid‐based surfactants was investigated. Low yields (2–9%) were obtained in the acylation of free amino acids, such as l‐serine and l‐lysine, as well as their ethyl esters and amides with fatty acids, owing in part to low miscibility of the reactants. When the N‐carbobenzyloxy (Cbz)‐l‐amino acids were used in an effort to improve miscibility of the amino acid derivatives with the acyl donor, a dramatic improvement was observed for N‐Cbz‐l‐serine (92% yield) but not for Nα‐Cbz‐ or Nζ‐Cbz‐l‐lysine (7 and 2% yield, respectively). As an alternative, and efficient synthesis of Nζ‐acyl‐l‐lysines was developed, based on the regiospecific chemical acylation of copper(II) lysinate. In pursuit of a general route to amino acid‐fatty acid surfactants, the utility of a polyol linker was investigated. Thus, the glycerol ester of Nα′Nζ‐di‐Cbz‐l‐lysine was prepared and evaluated as a substrate for acylation. As expected, this and other glycer‐1‐yl esters of N‐protected amino acids were excellent substrates for lipase‐catalyzed acylation. Their reaction with myristic acid in the presence of Novozyme resulted in the regioselective acylation of the primary hydroxyl group of the glycerol moiety to afford the corresponding 1‐O‐(N‐Cbz‐l‐aminoacyl)‐3‐O‐myris‐toylglycerols with conversions of 50–90%. These were readily deprotected to give a range of 1‐O‐(aminoacyl)‐3‐O‐myristoyl‐glycerols with overall yields of 27–71%.

  DOI：

  10.1007/s11746-997-0232-8