benzyl (2S,3S)-2-azido-5-(1,3-dioxoisoindol-2-yl)-3-hydroxypentanoate | 307494-02-6

• 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: benzyl (2S,3S)-2-azido-5-(1,3-dioxoisoindol-2-yl)-3-hydroxypentanoate
• CAS: 307494-02-6
• 化学式: C₂₀H₁₈N₄O₅
• 分子量: 394.387
• InChiKey: PBNAYICSDDINFT-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S)-2-azido-5-(1,3-dioxoisoindol-2-yl)-3-hydroxypentanoate 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Thalidomide metabolites and analogs. Part 2: Cyclic derivatives of 2-N-phthalimido-2S,3S (3-hydroxy) ornithine

  摘要：

  E-(5-N-phthaloyl)-2-pentenoic acid benzyl ester was dihydroxylated by a Sharpless AD-mix protocol followed by mononosylation of the resultant 2R,3S diol. Azide displacement of the mononosylate followed by protection with the TBDMS group gave the epsilon-N-phthaloyl-substituted-beta-tert-butyldimethylsilyloxy-alpha-azidocarboxylic acid benzylester. Hydrazinolysis resulted in removal of the phthalimide group with concomitant lactamization to the 4-silyloxy-3-azidopiperidinones. Staudinger reduction of the azidopiperidinones followed by N-phthaloylation and hydrolysis of the silyl group afforded the 4'-hydroxylated-6'-deoxythalidomide derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01204-1
• 作为产物：
  描述：

  (苄氧羰基甲基)三苯基溴化膦 在 sodium hydroxide 、 AD-mix-α 、 sodium azide 、 甲基磺酰胺 、 三乙胺 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 132.0h， 生成 benzyl (2S,3S)-2-azido-5-(1,3-dioxoisoindol-2-yl)-3-hydroxypentanoate
  参考文献：
  名称：

  Thalidomide metabolites and analogs. Part 2: Cyclic derivatives of 2-N-phthalimido-2S,3S (3-hydroxy) ornithine

  摘要：

  E-(5-N-phthaloyl)-2-pentenoic acid benzyl ester was dihydroxylated by a Sharpless AD-mix protocol followed by mononosylation of the resultant 2R,3S diol. Azide displacement of the mononosylate followed by protection with the TBDMS group gave the epsilon-N-phthaloyl-substituted-beta-tert-butyldimethylsilyloxy-alpha-azidocarboxylic acid benzylester. Hydrazinolysis resulted in removal of the phthalimide group with concomitant lactamization to the 4-silyloxy-3-azidopiperidinones. Staudinger reduction of the azidopiperidinones followed by N-phthaloylation and hydrolysis of the silyl group afforded the 4'-hydroxylated-6'-deoxythalidomide derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01204-1

文献信息

• Thalidomide metabolites and analogs. Part 2: Cyclic derivatives of 2-N-phthalimido-2S,3S (3-hydroxy) ornithine
  作者：Frederick A Luzzio、Elizabeth M Thomas、William D Figg

  DOI：10.1016/s0040-4039(00)01204-1

  日期：2000.9

  E-(5-N-phthaloyl)-2-pentenoic acid benzyl ester was dihydroxylated by a Sharpless AD-mix protocol followed by mononosylation of the resultant 2R,3S diol. Azide displacement of the mononosylate followed by protection with the TBDMS group gave the epsilon-N-phthaloyl-substituted-beta-tert-butyldimethylsilyloxy-alpha-azidocarboxylic acid benzylester. Hydrazinolysis resulted in removal of the phthalimide group with concomitant lactamization to the 4-silyloxy-3-azidopiperidinones. Staudinger reduction of the azidopiperidinones followed by N-phthaloylation and hydrolysis of the silyl group afforded the 4'-hydroxylated-6'-deoxythalidomide derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.