2-Oxo-3-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-propionic acid isopropyl ester | 366023-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Oxo-3-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-propionic acid isopropyl ester
• CAS: 366023-43-0
• 化学式: C₁₆H₂₆O₇
• 分子量: 330.378
• InChiKey: LYNUFHVRRDTYNR-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-Oxo-3-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-propionic acid isopropyl ester 在 palladium on activated charcoal 氢气 作用下， 以 异丙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 48.0h， 生成 2-Amino-3-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-propionic acid isopropyl ester
  参考文献：
  名称：

  Synthesis of new glycosyl-α-aminoacid derivatives for glycopeptide chemistry

  摘要：

  The synthesis of new N- or C-protected glycosyl-alpha -aminoacids and their use to prepare new glycopeptides is described. The overall synthetic strategy to obtain these new alpha -aminoacid chirons involves four distinct steps from dialdoses: (1) a diastereoselective Darzens reaction between the potassium anion derived from isopropyl dichloroacetate and a suitable protected dialdose, (2) the one-pot transformation of the so-obtained isopropyl glycosyl-alpha -chloroglycidic ester with magnesium iodide, then sodium hydrogenosulfite, into an isopropyl glycosyl-alpha -ketoester, (3) the reductive amination of the alpha -ketoester with (S)-alpha -methylbenzylamine and an hydrogenating reagent, (4) N- or C-selective deprotection and further peptidic coupling. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00600-7
• 作为产物：
  描述：

  二氯乙酸异丙酯 在 potassium methanolate 、 magnesium iodide 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 2-Oxo-3-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-propionic acid isopropyl ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of mechanism-based inhibitors of KDO8P synthase and DAH7P synthase

  摘要：

  KDO8PS (3-deOXY-D-manno-2-octulosonate-8-phosphate synthase) and DAH7PS (3-deOXY-D-arabino-2-heptulosonate-7-phosphate synthase) are attractive targets for the development of new anti-infectious agents. Both enzymes appear to proceed via a common mechanism involving the reaction of phosphoenolpyruvate (PEP) with arabinose 5-phosphate or erythrose-4-phosphate, to produce the corresponding ulosonic acids, KDO8P and DAH7P, respectively. The synthesis of new inhibitors closely related to the supposed tetrahedral intermediate substrates for the enzymes is described. The examination of the antibacterial activity of these derivatives is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.019