tert-butyl (S)-1-[(S)-3-(tert-butoxycarbonylamino)-4-tert-butoxy-4-oxobutyl]azetidine-2-carboxylate | 187796-28-7

• 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: tert-butyl (S)-1-[(S)-3-(tert-butoxycarbonylamino)-4-tert-butoxy-4-oxobutyl]azetidine-2-carboxylate
• 英文别名: tert-butyl (2S)-1-[(3S)-4-[(2-methylpropan-2-yl)oxy]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutyl]azetidine-2-carboxylate
• CAS: 187796-28-7
• 化学式: C₂₁H₃₈N₂O₆
• 分子量: 414.543
• InChiKey: BFBKTWATXJLKCZ-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-1-[(S)-3-(tert-butoxycarbonylamino)-4-tert-butoxy-4-oxobutyl]azetidine-2-carboxylate 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 sodium cyanoborohydride 、 溶剂黄146 、 苯甲醚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 33.5h， 生成 (2S:3'S:3''S)-N-[N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl]-azetidine-2-carboxylic acid
  参考文献：
  名称：

  A New Efficient Synthesis of Nicotianamine and 2'-Deoxymugineic Acid

  摘要：

  Nicotianamine and 2'-deoxymugineic acid, phytosiderophores, have been efficiently synthesized, which will be suitable for large scale production of these plant physiologically important compounds. The synthetic method for 2',3 ''-dideoxy-3 ''-oxomugineic acid was also investigated.

  DOI：

  10.3987/com-96-s52
• 作为产物：
  描述：

  1-tert-butyl 4-methyl N-(tert-butyloxycarbonyl)-L-aspartate 在 4-二甲氨基吡啶 、 氯甲酸乙酯 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 丙酮 、 乙腈 为溶剂， 反应 70.0h， 生成 tert-butyl (S)-1-[(S)-3-(tert-butoxycarbonylamino)-4-tert-butoxy-4-oxobutyl]azetidine-2-carboxylate
  参考文献：
  名称：

  用于合成烟胺及其衍生物的 L-氮杂环丁烷-2-羧酸的多克级和无柱层析合成

  摘要：

  Multigram-scale synthesis of L-azetidine-2-carboxylic acid from L-aspartic acid was achieved in 13 conventional synthetic steps, without the need for purification by silica-gel column chromatography and expensive reagents. Nicotianamine and its fluorescence-labeled derivatives could be obtained from this synthetic strategy.

  DOI：

  10.3987/com-18-14002

文献信息

• A Novel Synthetic Approach Towards Phytosiderophores: Expeditious Synthesis of Nicotianamine and 2′-Deoxymugineic Acid
  作者：Sukhbinder S Klair、Hindupur R Mohan、Takeshi Kitahara

  DOI：10.1016/s0040-4039(97)10496-8

  日期：1998.1

  A short and a novel approach for synthesis of nicotianamine, 2′-deoxymugineic acid and related phytosiderophores has been achieved through peptide intermediates. Selective amide reduction in the presence of ester functionalities by conversion to thioamide and subsequent desulfurization with Raney nickel were employed as key reactions. © 1997 Elsevier Science Ltd. All rights reserved.

  通过肽中间体已经实现了一种短而新颖的合成烟碱胺，2'-脱氧ugineic酸和相关植物铁载体的方法。在酯官能度存在下通过转化成硫酰胺的选择性酰胺还原反应以及随后与阮内镍的脱硫反应被用作关键反应。©1997 Elsevier ScienceLtd。保留所有权利。
• WO2023/190156
  申请人：——

  公开号：——

  公开（公告）日：——
• Multigram-Scale and Column Chromatography-Free Synthesis of L-Azetidine-2-carboxylic Acid for the Synthesis of Nicotianamine and Its Derivatives
  作者：Minoru Izumi、Tomohiro Takaishi、Kyosuke Wakisaka、Christopher J Vavricka、Hiromasa Kiyota

  DOI：10.3987/com-18-14002

  日期：——

  Multigram-scale synthesis of L-azetidine-2-carboxylic acid from L-aspartic acid was achieved in 13 conventional synthetic steps, without the need for purification by silica-gel column chromatography and expensive reagents. Nicotianamine and its fluorescence-labeled derivatives could be obtained from this synthetic strategy.
• A New Efficient Synthesis of Nicotianamine and 2'-Deoxymugineic Acid
  作者：Takayuki Shioiri、Naoko Irako、Sachiko Sakakibara、Fumiyoshi Matsuura、Yasumasa Hamada

  DOI：10.3987/com-96-s52

  日期：——

  Nicotianamine and 2'-deoxymugineic acid, phytosiderophores, have been efficiently synthesized, which will be suitable for large scale production of these plant physiologically important compounds. The synthetic method for 2',3 ''-dideoxy-3 ''-oxomugineic acid was also investigated.