N-acetylthreonine ethyl 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: N-acetylthreonine ethyl ester
• 英文别名: (+/-)-threo-2-Acetamino-3-hydroxy-buttersaeure-aethylester；N-Acetyl-threonin-aethylester；ethyl (2R,3S)-2-acetamido-3-hydroxybutanoate
• 化学式: C₈H₁₅NO₄
• 分子量: 189.211
• InChiKey: BGBUNNHXCHSBQT-CAHLUQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetylthreonine ethyl ester 在 盐酸 作用下， 反应 3.0h， 生成 D-苏氨酸
  参考文献：
  名称：

  对映体合成L-苏氨酸

  摘要：

  L-苏氨酸的对映体选择性合成

  DOI：

  10.1002/hlca.19870700128
• 作为产物：
  描述：

  3-oxo-2-(phenylhydrazono)butyric acid ethyl ester 在 溶剂黄146 、 铂 、 锌 作用下， 生成 N-acetylthreonine ethyl ester
  参考文献：
  名称：

  Pfister et al., Journal of the American Chemical Society, 1949, vol. 71, p. 1101,1103

  摘要：

  DOI：

文献信息

• Catalytic process for preparing optically active threonine
  申请人：Takasago International Corporation

  公开号：EP0322236A2

  公开（公告）日：1989-06-28

  A 2-N-acylaminoacetoacetic ester represented by the formula: wherein R1 represents lower alkyl, or phenyl or benzyl each of which may be substituted with lower alkyl group or lower alkoxy; R2 represents hydrogen, a lower alkyl, lower alkoxy, or phenyl or benzyloxy, each of which may be substituted with lower alkyl or lower alkoxy, is dissolved in a solvent (e.g. an alkanol), mixed with a ruthenium-optically active phosphine complex as a catalyst, and hydrogenated at 25 to 50°C at a H2 pressure of 10-100 kg/cm2 for 15 to 48 hours, to obtain as an intermediate an optically active N-acyl threonine represented by: wherein R1 and R2 are as defined above. The intermediate (II) can be selectively prepared in a high yield and is then hydrolysed with HCI to obtain optically active threonine (CH3CHOHCHNH2COOH). Natural or non-natural type threonine can be prepared selectively by seleoting the absolute configuration of the ligand of the ruthenium-optically active phosphine complex, of which four general formulae are given, all containing a "BINAP" tertiary phosphine; syntheses of the catalyst are given.

  一种 2-N-酰氨基乙酰乙酸酯，由式表示： 其中 R1 代表低级烷基，或苯基或苄基，它们各自可被低级烷基或低级烷氧基取代； R2 代表氢、低级烷基、低级烷氧基或苯基或苄氧基，它们各自可被低级烷基或低级烷氧基取代。例如烷醇）中，与作为催化剂的钌-光学活性膦络合物混合，并在 25 至 50℃、10-100 kg/cm2 的 H2 压力下氢化 15 至 48 小时，以获得光学活性 N-酰基苏氨酸作为中间体： 其中 R1 和 R2 如上定义。 中间体（II）可以选择性地以高产率制备，然后用 HCI 进行水解，得到光学活性苏氨酸（CH3CHOHCHNH2COOH）。通过选择钌-光学活性膦配合物配体的绝对构型，可以选择性地制备天然或非天然苏氨酸，其中给出了四个通式，均含有 "BINAP "叔膦，并给出了催化剂的合成方法。
• Asymmetric synthesis. Practical production of D and L threonine. Dynamic kinetic resolution in rhodium and ruthenium catalyzed hydrogenation of 2-acylamino-3-oxobutyrates.
  作者：J.P. Genet、C. Pinel、S. Mallart、S. Juge、S. Thorimbert、J.A. Laffitte

  DOI：10.1016/s0957-4166(00)86108-x

  日期：1991.1

  Enantioselective syntheses of D and L threonine are described. Racemic methyl and ethyl 2-acylamino-3-oxobutyrate 1 were synthesized from the corresponding acetoacetates 6 and then hydrogenated stereoselectively via dynamic kinetic resolution with various chiral P * P Rh (I) 8 and Ru (II) 10 catalysts to give syn optically active alcohols which could be converted by hydrolysis and treatment with propylene oxide into threonine. The best results were obtained using (-) CHIRAPHOS Ru and (+) BINAP Ru as catalysts, in the hydrogenation step leading respectively to D threonine (ee: 99 %) and L threonine (ee: 94 %) in 26-34 % overall yields.
• THE TOTAL SYNTHESIS OF SPARTEINE
  作者：Nelson J. Leonard、Roger E. Beyler

  DOI：10.1021/ja01186a522

  日期：1948.6
• Catalytic hydrogenation of ethyl ?-acetylamino-?-ketobutyrate on modified metal catalysts
  作者：I. P. Murina、A. A. Vedenyapin、E. I. Klabunovskii

  DOI：10.1007/bf00957047

  日期：1988.5
• Kato, Nobuo; Fujie, Masayoshi; Hasegawa, Masayasu, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 2, p. 303 - 307
  作者：Kato, Nobuo、Fujie, Masayoshi、Hasegawa, Masayasu、Shimao, Masayuki、Kita, Keiko、Yanase, Hideshi

  DOI：——

  日期：——