(3R,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone | 137694-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone
• 英文别名: benzyl N-[(4R,7S)-3,6-dioxo-5-oxa-2-azaspiro[3.5]nonan-7-yl]carbamate
• CAS: 137694-52-1
• 化学式: C₁₅H₁₆N₂O₅
• 分子量: 304.302
• InChiKey: VEIBIFSLOALVRS-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 (S)-2-Benzyloxycarbonylamino-4-((R)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid
  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
• 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 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone
  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