(2r,3r)-2-Amino-3-methyl-4-pentenoic acid

• 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: (2r,3r)-2-Amino-3-methyl-4-pentenoic acid
• 英文别名: (2R,3R)-2-amino-3-methylpent-4-enoic acid
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: RXVINEUKGZXZAV-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  benzyl (2RS,3RS)-1-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-3-methyl-1-oxopent-4-en-2-ylcarbamate 在 氢气 、 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 (2r,3r)-2-Amino-3-methyl-4-pentenoic acid
  参考文献：
  名称：

  抗β-取代的γ，δ-不饱和氨基酸的不对称Eschenmoser-Claisen重排。

  摘要：

  光学活性的抗β-取代的γ，δ-不饱和氨基酸是有机合成和拟肽过程中重要的合成基石。一种新型的不对称Eschenmoser-Claisen重排使用C2对称手性助剂被开发来生成这种类型的氨基酸。通过碘代内酯化/锌还原除去手性助剂后，获得了极好的非对映选择性和高对映选择性（87-93％ee）。

  DOI：

  10.1021/ol701704h

文献信息

• [EN] SYNTHESIS OF (2S,3R,4R)-4,5-DIHYDROXYISOLEUCINE AND DERIVATIVES<br/>[FR] SYNTHÈSE DE (2S,3R,4R)-4,5-DIHYDROXYISOLEUCINE ET DE SES DÉRIVÉS
  申请人：HEIDELBERG PHARMA RES GMBH

  公开号：WO2019185877A1

  公开（公告）日：2019-10-03

  The invention relates to a method for the preparation of a 4,5-dihydroxyisoleucine derivative comprising the steps of asymmetric Claisen rearrangement of a Z-aminocrotyl-glycin ester and subsequent kinetic resolution of the product diastereomer mix by acylase, and subsequent Sharpless dihydroxylation of the resulting 2-amino-3-methylpent-4-enoicacid derivative.

  该发明涉及一种制备4,5-二羟基异亮氨酸衍生物的方法，包括Z-氨基环丙基甘氨酸酯的不对称克莱森重排步骤，随后通过酰化酶对产物对映体混合物进行动力学拆分，以及随后对所得的2-氨基-3-甲基戊-4-烯酸衍生物进行夏普利斯二羟基化的步骤。
• SYNTHESIS OF (2S,3R,4R)-4,5-DIHYDROXYISOLEUCINE AND DERIVATIVES
  申请人：Heidelberg Pharma GmbH

  公开号：EP3546447A1

  公开（公告）日：2019-10-02

  The invention relates to a method for the preparation of a 4,5-dihydroxyisoleucine derivative comprising the steps of asymmetric Claisen rearrangement of a Z-aminocrotyl-glycin ester and subsequent kinetic resolution of the product diastereomer mix by acylase, and subsequent Sharpless dihydroxylation of the resulting 2-amino-3-methylpent-4-enoicacid derivative

  本发明涉及一种制备 4,5-二羟基异亮氨酸衍生物的方法，该方法包括以下步骤：Z-氨基丙烯酰-甘氨酸酯的不对称克莱森重排，随后通过酰化酶对产物非对映异构体混合进行动力学解析，以及随后对得到的 2-氨基-3-甲基戊-4-烯酸衍生物进行 Sharpless 二羟基化反应。
• Asymmetric β‐Methylation of <scp>l</scp> ‐ and <scp>d</scp> ‐α‐Amino Acids by a Self‐Contained Enzyme Cascade
  作者：Cangsong Liao、Florian P. Seebeck

  DOI：10.1002/anie.201916025

  日期：2020.4.27

  AbstractThis report describes a modular enzyme‐catalyzed cascade reaction that transforms l‐ or d‐α‐amino acids to β‐methyl‐α‐amino acids. In this process an α‐amino acid transaminase, an α‐keto acid methyltransferase, and a halide methyltransferase cooperate in two orthogonal reaction cycles that mediate product formation and regeneration of the cofactor pyridoxal‐5′‐phosphate and the co‐substrate S‐adenosylmethionine. The only stoichiometric reagents consumed in this process are the unprotected l‐ or d‐α‐amino acid and methyl iodide.
• Synthesis of (2S,3R,4R)-4,5-Dihydroxyisoleucine and Derivatives
  申请人：Heidelberg Pharma Research GmbH

  公开号：US20210009507A1

  公开（公告）日：2021-01-14

  The invention relates to a method for the preparation of a 4,5-dihydroxyisoleucine derivative comprising the steps of asymmetric Claisen rearrangement of a Z-aminocrotyl-glycin ester and subsequent kinetic resolution of the product diastereomer mix by acylase, and subsequent Sharpless dihydroxylation of the resulting 2-amino-3-methylpent-4-enoic acid derivative.
• Asymmetric Eschenmoser−Claisen Rearrangement for Anti-β-Substituted γ,δ-Unsaturated Amino Acids
  作者：Hongchang Qu、Xuyuan Gu、Zhihua Liu、Byoung J. Min、Victor J. Hruby

  DOI：10.1021/ol701704h

  日期：2007.9.1

  synthetic building blocks in organic synthesis and for peptidomimetics. A novel asymmetric Eschenmoser-Claisen rearrangement with use of a C2-symmetric chiral auxiliary was developed to generate this type of amino acid. Excellent diastereoselectivities and high enantioselectivities (87-93% ee) were obtained after the chiral auxiliary was removed via iodolactonization/zinc reduction.

  光学活性的抗β-取代的γ，δ-不饱和氨基酸是有机合成和拟肽过程中重要的合成基石。一种新型的不对称Eschenmoser-Claisen重排使用C2对称手性助剂被开发来生成这种类型的氨基酸。通过碘代内酯化/锌还原除去手性助剂后，获得了极好的非对映选择性和高对映选择性（87-93％ee）。