benzyl (2S,3S)-2-azido-3-[tert-butyl(dimethyl)silyl]oxy-5-(1,3-dioxoisoindol-2-yl)pentanoate | 307494-03-7

• 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: benzyl (2S,3S)-2-azido-3-[tert-butyl(dimethyl)silyl]oxy-5-(1,3-dioxoisoindol-2-yl)pentanoate
• CAS: 307494-03-7
• 化学式: C₂₆H₃₂N₄O₅Si
• 分子量: 508.649
• InChiKey: QBDNNLPFCVODCE-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S)-2-azido-3-[tert-butyl(dimethyl)silyl]oxy-5-(1,3-dioxoisoindol-2-yl)pentanoate 在 4-二甲氨基吡啶 、 三乙胺 、 三苯基膦 、 肼 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 38.0h， 生成 (R)-N-[(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-oxo-piperidin-3-yl]-3,3,3-trifluoro-2-methoxy-2-phenyl-propionamide
  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：

  3-邻苯二甲酰亚胺丙醛 在 2,4,6-三甲基吡啶 、 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 144.0h， 生成 benzyl (2S,3S)-2-azido-3-[tert-butyl(dimethyl)silyl]oxy-5-(1,3-dioxoisoindol-2-yl)pentanoate
  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