Acetic acid (2R,3aR,7R,7aR)-6-oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester | 102790-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: Acetic acid (2R,3aR,7R,7aR)-6-oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
• CAS: 102790-69-2
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: LRQODMKDSYMFRI-HKUMRIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3aR,7R,7aR)-6-oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 在 samarium diiodide 、 乙二醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以92%的产率得到3,4-O-(S)-benzylidene-2-deoxy-D-ribono-1,5-lactone
  参考文献：
  名称：

  A practical synthesis of 2-deoxy aldonolactones via a SmI2-mediated α-deoxygenation reaction

  摘要：

  A one-step deoxygenation of 2-hydroxylactones or their acetates is possible using samarium diiodide as an electron-transfer reagent in conjunction with a proton source.

  DOI：

  10.1016/s0040-4039(00)92313-x
• 作为产物：
  描述：

  卡培他滨杂质25 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 2.92h， 生成 Acetic acid (2R,3aR,7R,7aR)-6-oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
  参考文献：
  名称：

  Molecular Sieves Mediated Green Per-O-Acetylation of Carbohydrate Templates and Lipase Catalyzed Regioselective Alcoholysis of 2,3,5-Tri-O-Acetyl-D-Ribonolactone

  摘要：

  The per-O-acetylation of D-ribono-1,4-lactone and representative carbohydrates through the combination of acetic anhydride and molecular sieves under solvent-free conditions is demonstrated. The use of 13X/KCl molecular sieves as the heterogeneous catalyst was found to be more efficient than the excess of pyridine normally employed in the conventional method, giving high yields of the expected peracetylated product after 3 h at 25 degrees C or 1 h at 50 degrees C. The transformation can be carried out in gram scale and in an open flask. Additionally, the catalyst is readily separated from the reaction medium and can be reutilized without significant loss of activity. This green procedure for acetylation was extended to D-ribonolactone derivatives and natural carbohydrates. To demonstrate the synthetic utility of the method, 2,3,5-tri-O-acetyl-D-ribonolactone was selected as the substrate for the regioselective alcoholysis of acetyl group catalyzed by Candida antarctica lipase B in EtOH to selectively produce 2,3-di-O-acetyl-D-ribonolactone in gram scale.

  DOI：

  10.5935/0103-5053.20150037

文献信息

• Clarifying the Use of Benzylidene Protecting Group for D-(+)-Ribono-1,4-Lactone, an Essential Building Block in the Synthesis of C-Nucleosides
  作者：Silvana Casati、Paola Rota、Pietro Allevi、Alessandra Mingione、Roberta Ottria、Pierangela Ciuffreda

  DOI：10.3390/molecules26216447

  日期：——

  have been the subject of renewed interest from the scientific community thanks to their antiviral activity. The COVID-19 global pandemic, indeed, spread light on the antiviral drug Remdesivir, an adenine C-nucleoside analogue. This new attention of the medical community on Remdesivir prompts the medicinal chemists to investigate once again C-nucleosides. One of the essential building blocks to synthetize

  在过去的两年中，核苷类似物是一类成熟的生物活性化合物，由于其抗病毒活性，已成为科学界重新关注的主题。COVID-19 全球大流行确实让人们对抗病毒药物瑞德西韦（一种腺嘌呤C核苷类似物）有所了解。医学界对瑞德西韦的这种新关注促使药物化学家再次研究C-核苷。合成这些化合物的基本组成部分之一是 D-(+)-ribono-1,4-内酯，但与使用不同碳水化合物保护基团相关的一些机制方面仍不清楚。在这里，我们介绍了我们对使用亚苄基作为核糖内酯保护基团的研究，这些保护基团可用于合成C-嘌呤核苷类似物。提供了在不同反应条件下获得的化合物的详细 1D 和 2D NMR 结构研究。此外，使用 CHCl 3和 DMSO的 SM8 溶剂化模型在 B3LYP/6-31G* 理论水平进行分子建模研究，以支持获得的结果。该研究允许澄清机理方面，因为副反应和结构重排喜欢使用亚苄基保护基团。