anti-(2R,3R)-Methyl 2-(benzamidomethyl)-3-hydroxybutanoate | 135138-76-0

• 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: anti-(2R,3R)-Methyl 2-(benzamidomethyl)-3-hydroxybutanoate
• 英文别名: (2R,3R)-methyl-2-benzamido-methyl-3-hydroxybutyrate；(2R,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate；methyl (2R,3R)-2-(benzamidomethyl)-3-hydroxybutanoate
• CAS: 135138-76-0
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: ATBIFOORFZTUKF-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (2S,3R)-2-[(苯甲酰基氨基)甲基]-3-羟基丁酸甲酯 、 anti-(2R,3R)-Methyl 2-(benzamidomethyl)-3-hydroxybutanoate 以gave primarily the (2R,3R) stereoisomer的产率得到甲基2-[(苯甲酰基氨基)甲基]-3-氧代丁酸酯
  参考文献：
  名称：

  KETOREDUCTASE POLYPEPTIDES FOR THE PRODUCTION OF AZETIDINONE

  摘要：

  本公开提供了经过改良的酮还原酶酶，其性质比自然存在的野生型酮还原酶酶有所改善。同时，还提供了编码经过改良的酮还原酶酶的多核苷酸、能够表达经过改良的酮还原酶酶的宿主细胞以及使用经过改良的酮还原酶酶合成各种手性化合物的方法。

  公开号：

  US20150197731A1
• 作为产物：
  描述：

  甲基2-[(苯甲酰基氨基)甲基]-3-氧代丁酸酯 在 I 氢气 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、5.07 MPa 条件下， 反应 20.0h， 生成 (2S,3R)-2-[(苯甲酰基氨基)甲基]-3-羟基丁酸甲酯 、 anti-(2R,3R)-Methyl 2-(benzamidomethyl)-3-hydroxybutanoate
  参考文献：
  名称：

  Cationic BINAP-Ru(II) Halide Complexes: Highly Efficient Catalysts for Stereoselective Asymmetric Hydrogenation of .alpha.- and .beta.-Functionalized Ketones

  摘要：

  Cationic ruthenium-BINAP complexes 5, 7, and 10 of the formula [RuX((S)-BINAP) (arene)]Y, where X = Cl, Br, I; Y = Cl, Br, I, BF4, B(C6H5)(4); arene = benzene, p-cymene, ethyl benzoate, and their enantiomers have been prepared by the reaction of arene-ruthenium halide complexes 4, 6, and 9 with (S)-BINAP or (R)-BINAP. Structures of the complexes were established by spectroscopy, conductivity, and a single-crystal X-ray analysis (5d: orthorhombic, P2(1)2(1)2; a 20.141(2) Angstrom, b = 18.504(1) Angstrom, c 12.241(1) Angstrom V = 4562.0(7) Angstrom(3), Z = 4, R = 0.078 for unique 4177 reflections). BINAP derivatives with various substituents at the para and meta positions of four phenyl rings on phosphorus atoms and their cationic Ru(II) complexes have also been synthesized. These BINAP-Ru(II) complexes have been used as catalysts for the asymmetric hydrogenation of various unsaturated organic compounds such as alpha- and beta-keto esters, allylic alcohols, and alpha,beta-unsaturated carboxylic acids in excellent diastereo- and/or enantioselectivities. Catalytic activities and stereoselectivities depend highly on reaction conditions such as solvent, temperature, and additives. Variation of halogen ligands bound to ruthenium atom and substituents on four phenyl rings of BINAP also have exerted remarkable effects on the efficiency of the catalysis. Asymmetric hydrogenation of methyl (+/-)-2-(benzamidomethyl)-3-oxobutanoate catalyzed by the species derived from 9c and 3,5((t)Bu)(2)-BINAP afforded the corresponding syn-(2S,3R)-17 in 98% de and 99% ee.

  DOI：

  10.1021/jo00090a026

文献信息

• Stereoselective hydrogenation via dynamic kinetic resolution
  作者：R. Noyori、T. Ikeda、T. Ohkuma、M. Widhalm、M. Kitamura、H. Takaya、S. Akutagawa、N. Sayo、T. Saito、T. Taketomi、H. Kumobayashi

  DOI：10.1021/ja00207a038

  日期：1989.12.1

  Stereoselectivite dans l'hydrogenation de cetoesters et d'un aminoester conjugue, catalysee par des complexes du ruthenium

  Stereoselectivite dans l'hydrogenation de cetoesters et d'unaminoester conjugue, catalysee par des complexes du ruthenium
• COPPER CATALYZED HALOGENATON AND REACTION PRODUCTS
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20140371480A1

  公开（公告）日：2014-12-18

  A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring a halogen from an sp 2 to a benzylic carbon with good enantioselectivity and concomitant borylation of the Ar-halo bond. The resulting enantio-enriched benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom or carbon-carbon bond while maintaining high ee. The reaction can be used to efficiently prepare novel compounds and intermediates for the preparation of therapeutics and ligands for catalysis.

  一种Cu(I)催化的1,3-卤迁移反应有效地通过将卤素从sp2转移到苄基碳来循环利用一个活化基团，具有良好的对映选择性并伴随Ar-卤键的硼化反应。所得的对映富集的苄基卤化物可以在同一容器中在各种条件下反应，形成额外的碳-杂原子或碳-碳键，同时保持高的ee。该反应可用于高效制备新型化合物和制备治疗剂和催化剂配体的中间体。
• Ketoreductase Polypeptides for the Production of Azetidinone
  申请人：Campopiano Onorato

  公开号：US20090162909A1

  公开（公告）日：2009-06-25

  The present disclosure provides engineered ketoreductase enzymes having improved properties as compared to a naturally occurring wild-type ketoreductase enzyme. Also provided are polynucleotides encoding the engineered ketoreductase enzymes, host cells capable of expressing the engineered ketoreductase enzymes, and methods of using the engineered ketoreductase enzymes to synthesize a variety of chiral compounds.

  本公开提供了经过改良的酮还原酶酶，其性能比自然存在的野生型酮还原酶酶有所提高。还提供了编码经过改良的酮还原酶酶的多核苷酸，能够表达经过改良的酮还原酶酶的宿主细胞，以及使用经过改良的酮还原酶酶合成各种手性化合物的方法。
• KETOREDUCTASE POLYPEPTIDES FOR THE PRODUCTION OF AZETIDINONE
  申请人：Campopiano Onorato

  公开号：US20110159567A1

  公开（公告）日：2011-06-30

  The present disclosure provides engineered ketoreductase enzymes having improved properties as compared to a naturally occurring wild-type ketoreductase enzyme. Also provided are polynucleotides encoding the engineered ketoreductase enzymes, host cells capable of expressing the engineered ketoreductase enzymes, and methods of using the engineered ketoreductase enzymes to synthesize a variety of chiral compounds.

  本公开提供了经过改良的酮还原酶酶，其性质比自然存在的野生型酮还原酶酶更好。同时提供编码改良酮还原酶酶的多核苷酸，能够表达改良酮还原酶酶的宿主细胞，以及使用改良酮还原酶酶合成各种手性化合物的方法。
• Ketoreductases
  申请人：C-LEcta GmbH

  公开号：US10093905B2

  公开（公告）日：2018-10-09

  The invention relates to ketoreductases and the use thereof. The ketoreductases of the invention are particularly useful for enzymatically catalyzing the reduction of ketones to chiral secondary alcohols.

  本发明涉及酮还原酶及其用途。本发明的酮还原酶特别适用于酶催化酮还原成手性仲醇。