(3R,4R,7R)-8-(tert-butoxycarbonyl)-7-methoxycarbonyl-3-phenyl-2-(phenylmethyl)-5-thia-2,8-diazaspiro[3,4]octan-1-one | 872051-54-2

• 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: (3R,4R,7R)-8-(tert-butoxycarbonyl)-7-methoxycarbonyl-3-phenyl-2-(phenylmethyl)-5-thia-2,8-diazaspiro[3,4]octan-1-one
• 英文别名: 8-O-tert-butyl 7-O-methyl (1R,4R,7R)-2-benzyl-3-oxo-1-phenyl-5-thia-2,8-diazaspiro[3.4]octane-7,8-dicarboxylate
• CAS: 872051-54-2
• 化学式: C₂₅H₂₈N₂O₅S
• 分子量: 468.574
• InChiKey: VMZAYOOARPCCSJ-WZOHSFFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4R,7R)-8-(tert-butoxycarbonyl)-7-methoxycarbonyl-3-phenyl-2-(phenylmethyl)-5-thia-2,8-diazaspiro[3,4]octan-1-one 在 盐酸 作用下， 以 氯仿 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 84.0h， 生成 (4R)-4-phenyl-1-(phenylmethyl)azetidine-2,3-dione
  参考文献：
  名称：

  Asymmetric synthesis of 1,3-thiazolidine-derived spiro-β-lactams via a Staudinger reaction between chiral ketenes and imines

  摘要：

  Enantiomerically pure 1,3-thiazolidine-derived spiro-beta-lactams were stereoselectively synthesised by means of a Staudinger ketene-imine reaction starting from optically active N-Boc-1,3-thiazolidine-2-carboxylic acid derivatives and imines. The reactions were stereoselective and afforded spiro-beta-lactams with a relative trans-configuration. The absolute configuration of the new stereocentres was assigned on the basis of the well-accepted mechanism and confirmed by means of the X-ray crystal structure analysis. The spiro-beta-lactams were transformed into enantiomerically pure chiral monocyclic beta-lactams by opening the thiazolidine ring and recovering the chiral auxiliary. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.054
• 作为产物：
  描述：

  (2S,4R)-1,3-thiazolidine-2,3,4-tricarboxylic acid 3-(1,1-dimethylethyl) ester 4-methyl ester 、 (E)-N-benzylidenebenzylamine 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以40.5%的产率得到(3R,4R,7R)-8-(tert-butoxycarbonyl)-7-methoxycarbonyl-3-phenyl-2-(phenylmethyl)-5-thia-2,8-diazaspiro[3,4]octan-1-one
  参考文献：
  名称：

  Asymmetric synthesis of 1,3-thiazolidine-derived spiro-β-lactams via a Staudinger reaction between chiral ketenes and imines

  摘要：

  Enantiomerically pure 1,3-thiazolidine-derived spiro-beta-lactams were stereoselectively synthesised by means of a Staudinger ketene-imine reaction starting from optically active N-Boc-1,3-thiazolidine-2-carboxylic acid derivatives and imines. The reactions were stereoselective and afforded spiro-beta-lactams with a relative trans-configuration. The absolute configuration of the new stereocentres was assigned on the basis of the well-accepted mechanism and confirmed by means of the X-ray crystal structure analysis. The spiro-beta-lactams were transformed into enantiomerically pure chiral monocyclic beta-lactams by opening the thiazolidine ring and recovering the chiral auxiliary. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.054

文献信息

• Asymmetric synthesis of 1,3-thiazolidine-derived spiro-β-lactams via a Staudinger reaction between chiral ketenes and imines
  作者：Giuseppe Cremonesi、Piero Dalla Croce、Francesco Fontana、Alessandra Forni、Concetta La Rosa

  DOI：10.1016/j.tetasy.2005.08.054

  日期：2005.10

  Enantiomerically pure 1,3-thiazolidine-derived spiro-beta-lactams were stereoselectively synthesised by means of a Staudinger ketene-imine reaction starting from optically active N-Boc-1,3-thiazolidine-2-carboxylic acid derivatives and imines. The reactions were stereoselective and afforded spiro-beta-lactams with a relative trans-configuration. The absolute configuration of the new stereocentres was assigned on the basis of the well-accepted mechanism and confirmed by means of the X-ray crystal structure analysis. The spiro-beta-lactams were transformed into enantiomerically pure chiral monocyclic beta-lactams by opening the thiazolidine ring and recovering the chiral auxiliary. (c) 2005 Elsevier Ltd. All rights reserved.