(R)-N-acetyl-α-methylleucine ethyl ester | 141784-95-4

• 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: (R)-N-acetyl-α-methylleucine ethyl ester
• 英文别名: ethyl (R)-N-acetyl-alpha-methylleucinate；ethyl (2R)-2-acetamido-2,4-dimethylpentanoate
• CAS: 141784-95-4
• 化学式: C₁₁H₂₁NO₃
• 分子量: 215.293
• InChiKey: JUAMNKPHUGZQHO-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (2S)-2-isobutyl-2-methyl-3-[(1S,2S)-2-hydroxycyclohexyloxy]-3-butenoate 在 sodium azide 、 甲烷磺酸 、 三氟化硼乙醚 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 9.0h， 生成 (R)-N-acetyl-α-methylleucine ethyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids Using (S,S)-Cyclohexane-1,2-diol as a Chiral Auxiliary

  摘要：

  Diastereoselective alkylation of ethyl 2-methyl- and/or 2-ethylacetoacetates using the (S,S)cyclohexane-1,2-diol as an acetal chiral auxiliary afforded enol ethers (2a-f and 5a-f) of 92 - > 95% de in 31-70% yields. Removal of the cyclohexane-l,2-diol with BF3-OEt2 afforded beta -keto esters (3 and 6) bearing a chiral quaternary carbon. The beta -keto esters could be easily converted into optically active alpha -methylated and/or alpha -ethylated alpha,alpha -disubstituted amino acids (12 and 13) in 21-99% yields using Schmidt rearrangement.

  DOI：

  10.1021/jo001423m

文献信息

• Enzymatic resolution of .alpha.-tertiary carboxylic acid esters
  申请人：Genzyme Corporation

  公开号：US05492830A1

  公开（公告）日：1996-02-20

  A method for the resolution of .alpha.-tertiary carboxylic acid esters by partial hydrolysis is disclosed. The partial hydrolysis is carried out by contacting the esters with an aqueous solution in the presence of a serine carboxypeptidase, and the hydrolysis product is separated from unreacted starting material to obtain the hydrolysis product or the unreacted starting material in enantiomerically enriched form. A novel ester hydrolase which is particularly useful in this method, and a nucleotide sequence encoding this enzyme, are also described.

  本发明揭示了一种通过部分水解来分离α-三级羧酸酯的方法。通过在丝氨酸羧肽酶存在下将酯与水溶液接触来进行部分水解，并将水解产物与未反应的起始物质分离，以获得具有对映体富集形式的水解产物或未反应的起始物质。本发明还描述了一种特别有用的酯水解酶及其编码这种酶的核苷酸序列。
• Biocatalytic resolution of tertiary .alpha.-substituted carboxylic acid esters: efficient preparation of a quaternary asymmetric carbon center
  作者：Christopher Yee、Todd A. Blythe、Thomas J. McNabb、Alan E. Walts

  DOI：10.1021/jo00039a004

  日期：1992.6

  A method for resolving a variety of tertiary alpha-substituted carboxylic acid
• EP1981831A2
  申请人：——

  公开号：EP1981831A2

  公开（公告）日：2008-10-22
• Kit for automated resolving agent selection and method thereof
  申请人：Vaidya A. Niteen

  公开号：US20070185346A1

  公开（公告）日：2007-08-09

  The present invention concerns an improved method and a tray or kit, which is useful to select quickly the optimum resolution agents, combinations and conditions to separate optical isomers. The tray of 24, 48, 96 or more samples is examined simultaneously visually or by standard analytical techniques.
• KIT FOR AUTOMATED RESOLVING AGENT SELECTION AND METHOD THEREOF
  申请人：Vaidya Niteen A.

  公开号：US20120041225A1

  公开（公告）日：2012-02-16

  The present invention provides a means for the rapid selection of optimum resolving agents and solvents, combinations and conditions to separate optical isomers. The present invention combinedly describes and automates a full lifecycle of chiral separation method development and optimization through a series of kits and procedures providing screening, automation for screening, racemate recovery, enantiomer preparation, and method optimization.