(S)-3-amino-1-benzyloxypiperidin-2-one hydrobromide

• 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)-3-amino-1-benzyloxypiperidin-2-one hydrobromide
• 英文别名: (3S)-3-amino-1-phenylmethoxypiperidin-2-one;hydrobromide
• 化学式: BrH*C₁₂H₁₆N₂O₂
• 分子量: 301.183
• InChiKey: DUZARYBXJMZRNT-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.64
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-amino-1-benzyloxypiperidin-2-one hydrobromide 在 三乙基硅烷 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 (S)-2-amino-N-[1-(benzyloxy)-2-oxopiperidin-3-yl]acetamide trifluoroacetate
  参考文献：
  名称：

  Synthesis of heterobactins A and B and Nocardia heterobactin

  摘要：

  The synthesis of the Rhodococcus erythropolis siderophores heterobactins A and B, and the structurally related Nocardia heterobactin, is described. Two approaches for the assembly of these asymmetric ligand donor chelators are explored. In the first approach, a scheme predicated on the biosynthesis of the Para coccus denitrificans siderophore, parabactin, is employed. In this approach, the central donor synthon is added last. In the second scheme, the central donor and the terminal 2,3-dihydroxybenzoyl fragment are first fixed to the ligand's D-ornithine backbone. This is followed by condensation with the cyclic ornithine hydroxamate glycine segment. The schemes offer a flexible approach to other heterobactins. Job's plots suggest that heterobactin A and Nocardia heterobactin form 1:1 ligand/metal complexes, while heterobactin B forms a 3:2 ligand/metal complex. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.003
• 作为产物：
  描述：

  (S)-3-benzyloxycarbonylamino-1-benzyloxy-2-piperidinone 在 氢溴酸 、 溶剂黄146 作用下， 以95%的产率得到(S)-3-amino-1-benzyloxypiperidin-2-one hydrobromide
  参考文献：
  名称：

  地精蛋白B的第一个全合成：链霉菌属菌种的混合配体铁载体。NRRL F-4415 †

  摘要：

  由链霉菌属菌种生产的结构多样的混合配体铁载体，戈比林B的第一个全合成。报告了NRRL F-4415。所述构建块的系统的组件以合成采空区-B 1第一半和采空区-B 2次使用导致gobichelin B的优异产率和纯度的隔离Pearlman催化剂这两个片段，随后整体去保护的半和随后的偶联。

  DOI：

  10.1039/c8ob00263k

文献信息

• The first total synthesis of gobichelin B: a mixed-ligand siderophore of<i>Streptomyces</i>sp. NRRL F-4415
  作者：Perali Ramu Sridhar、B. C. Venkatesh、Shaik Kalesha、Chalapala Sudharani

  DOI：10.1039/c8ob00263k

  日期：——

  The first total synthesis of a structurally diverse mixed ligand siderophore, gobichelin B produced by Streptomyces sp. NRRL F-4415, is reported. The systematic assembly of the building blocks to synthesize Gob-B 1st half and Gob-B 2nd half and subsequent coupling of these two fragments followed by global deprotection using Pearlman's catalyst led to the isolation of gobichelin B in excellent yield

  由链霉菌属菌种生产的结构多样的混合配体铁载体，戈比林B的第一个全合成。报告了NRRL F-4415。所述构建块的系统的组件以合成采空区-B 1第一半和采空区-B 2次使用导致gobichelin B的优异产率和纯度的隔离Pearlman催化剂这两个片段，随后整体去保护的半和随后的偶联。
• Total Synthesis of Exochelin MN and Analogues
  作者：Li Dong、Marvin J. Miller

  DOI：10.1021/jo0256078

  日期：2002.7.1

  The first total synthesis of exochelin MN is described along with rationally designed analogues. The required L-threo-beta-hydroxyamino acid components were constructed using either Sharpless asymmetric aminohydroxylation reactions or an aldol reaction of imidazolidinone 19. A new concise procedure for the preparation of the constituent six-membered cyclic hydroxamate was developed. In addition, a

  描述了exochelin MN的第一个全合成及其合理设计的类似物。所需的L-苏-β-羟基氨基酸组分是使用Sharpless不对称氨基羟基化反应或咪唑烷酮19的醛醇缩合反应构建的。开发了一种新的简洁方法，用于制备六元环状异羟肟酸酯。此外，提出了一种可行的机制，用于exochelin MN介导的铁（III）转运。这些化合物的生物学研究将用于评估该假设。
• Synthesis of heterobactins A and B and Nocardia heterobactin
  作者：Raymond J. Bergeron、Shailendra Singh、Neelam Bharti

  DOI：10.1016/j.tet.2011.03.003

  日期：2011.5

  The synthesis of the Rhodococcus erythropolis siderophores heterobactins A and B, and the structurally related Nocardia heterobactin, is described. Two approaches for the assembly of these asymmetric ligand donor chelators are explored. In the first approach, a scheme predicated on the biosynthesis of the Para coccus denitrificans siderophore, parabactin, is employed. In this approach, the central donor synthon is added last. In the second scheme, the central donor and the terminal 2,3-dihydroxybenzoyl fragment are first fixed to the ligand's D-ornithine backbone. This is followed by condensation with the cyclic ornithine hydroxamate glycine segment. The schemes offer a flexible approach to other heterobactins. Job's plots suggest that heterobactin A and Nocardia heterobactin form 1:1 ligand/metal complexes, while heterobactin B forms a 3:2 ligand/metal complex. (C) 2011 Elsevier Ltd. All rights reserved.
• Efforts toward the first total synthesis of a mixed‐ligand siderophore: Gobichelin‐A
  作者：Bhookya Shankar、Bhumireddy Chinnachennaiahgari Venkatesh、Perali Ramu Sridhar

  DOI：10.1002/psc.3525

  日期：2023.12

  The synthesis of Gobichelin-A, a naturally occurring mixed-ligand siderophore isolated from Streptomyces sp. NRRL F-4415, is described. The target molecule was planned to be synthesized by a convergent process involving the combination of two halves, Gob-A 1st half and Gob-A 2nd half, at the prefinal stage of the synthetic route. By adopting this method, fully protected Gobichelin-A was synthesized

  Gobichelin-A 的合成，这是一种从链霉菌中分离出来的天然存在的混合配体铁载体。描述了 NRRL F-4415。目标分子计划在合成路线的预最终阶段通过涉及两半（Gob-A 1st half 和 Gob-A 2nd half）组合的收敛过程来合成。采用该方法，以优异的产率合成了完全保护的戈比其林-A。