isotabtoxinine | 56599-17-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: isotabtoxinine
• 英文别名: tabtoxinine-δ-lactam；(2S,5S)-5-(azaniumylmethyl)-5-hydroxy-6-oxopiperidine-2-carboxylate
• CAS: 56599-17-8
• 化学式: C₇H₁₂N₂O₄
• 分子量: 188.183
• InChiKey: ROTDGSCRRKYCRZ-FFWSUHOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3S,3'S)-1-(tert-butyldimethylsilyl)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone 在 palladium on activated charcoal sodium hydroxide 、 四丁基氟化铵 、 水 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 25.0~37.0 ℃ 、101.33 kPa 条件下， 反应 7.5h， 生成 isotabtoxinine
  参考文献：
  名称：

  Enantiospecific synthesis of (-)-tabtoxinine .beta.-lactam

  摘要：

  A convergent, 10-step synthesis of optically active tabtoxinine beta-lactam [(-)-1] has been described. Key features of the synthetic route include (1) preparation of a new gamma-cation amino acid synthon, (-)-4, and its use as an electrophile (3 --> 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a. Synthons (-)-4 and 3 are available on a semipreparative scale.

  DOI：

  10.1021/jo00027a024

文献信息

• Synthesis of (-)-Tabtoxinine-β-lactam, the Phytotoxin of Tobacco Wildfire Disease
  作者：Hiromasa Kiyota、Takafumi Takai、Yasuharu Shimasaki、Masatoshi Saitoh、Osamu Nakayama、Tomoko Takada、Shigefumi Kuwahara

  DOI：10.1055/s-2007-983785

  日期：2007.8

  Synthesis of (-)-tabtoxinine-β-lactam and its (3R)-isomer, the cause of tobacco wildfire disease, was achieved from l-serine using a zinc-mediated coupling reaction, Sharpless asymmetric dihydroxylation and lactamization of β-mesyloxy benzylhydroxamate amide as the key steps.

  以 l-丝氨酸为原料，通过锌介导的偶联反应、Sharpless 不对称二羟基化反应和 δ-甲酰氧基苄基羟酰胺内酰胺化反应等关键步骤，合成了烟草野火病的致病物 (-)-tabtoxinine δ-内酰胺及其 (3R) 异构体。
• Enantiospecific synthesis of (-)-tabtoxinine .beta.-lactam
  作者：Roland E. Dolle、Chun Sing Li、Riccardo Novelli、Lawrence I. Kruse、Drake Eggleston

  DOI：10.1021/jo00027a024

  日期：1992.1

  A convergent, 10-step synthesis of optically active tabtoxinine beta-lactam [(-)-1] has been described. Key features of the synthetic route include (1) preparation of a new gamma-cation amino acid synthon, (-)-4, and its use as an electrophile (3 --> 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a. Synthons (-)-4 and 3 are available on a semipreparative scale.