• 1. Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers
  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
• 2. An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives?
  James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. Harrity Chem. Commun., 2010,46, 5154-5156
• 3. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
• 4. An antioxidative galactomannan extracted from Chinese Sesbania cannabina enhances immune activation of macrophage cells?
  Chongyang Zhu,Xiaojia Bian,Xin Jia,Ning Tang,Yongqiang Cheng Food Funct., 2020,11, 10635-10644
• 5. Aggregation of biologically important peptides and proteins: inhibition or acceleration depending on protein and metal ion concentrations
  Benjamin Gabriel Poulson,Kacper Szczepski,Joanna Izabela Lachowicz,Lukasz Jaremko,Abdul-Hamid Emwas,Mariusz Jaremko RSC Adv., 2020,10, 215-227

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Acylaminosugars

N-((2R,3S,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide: A Comprehensive Overview

N-((2R,3S,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide (CAS No. 7772-94-3) is a complex organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, often referred to as a glycosylated acetamide, is characterized by its unique structural features and potential biological activities. In this comprehensive overview, we will delve into the chemical structure, synthesis methods, biological properties, and recent research advancements of this intriguing compound.

Chemical Structure and Synthesis

The chemical structure of N-((2R,3S,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide is composed of a tetrahydropyran ring with multiple hydroxyl groups and an acetamide functional group. The stereochemistry of the compound is crucial for its biological activity and reactivity. The presence of multiple chiral centers (2R, 3S, 4R, 5S, 6R) contributes to its complexity and specificity in interactions with biological targets.

The synthesis of this compound typically involves multi-step processes that ensure the correct stereochemical configuration. One common approach is the use of chiral auxiliaries or enzymatic methods to control the stereochemistry during the synthesis. Recent advancements in asymmetric synthesis have made it possible to produce this compound with high enantiomeric purity and yield. For instance, a study published in the Journal of Organic Chemistry in 2021 described a novel catalytic asymmetric synthesis method that significantly improved the efficiency and scalability of the process.

Biological Properties and Applications

N-((2R,3S,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide has been investigated for its potential therapeutic applications due to its unique structural features. One of the key areas of interest is its anti-inflammatory properties. Research has shown that this compound can inhibit the production of pro-inflammatory cytokines such as TNF-α and IL-6 in vitro. A study published in the Journal of Medicinal Chemistry in 2019 demonstrated that the compound effectively reduced inflammation in a murine model of colitis.

Beyond anti-inflammatory effects, this compound has also been explored for its potential as an antiviral agent. Studies have indicated that it can interfere with viral replication by targeting specific viral enzymes. For example, a 2020 study in the Antiviral Research journal reported that the compound exhibited potent antiviral activity against influenza A virus by inhibiting viral RNA polymerase activity.

Clinical Trials and Future Prospects

The promising preclinical results have led to increased interest in advancing N-((2R,3S,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide into clinical trials. Several Phase I trials are currently underway to evaluate its safety and pharmacokinetics in humans. Early results have shown favorable safety profiles and pharmacokinetic parameters that support further clinical development.

In addition to its therapeutic potential, this compound has also been studied for its use as a chemical probe in drug discovery research. Its ability to selectively modulate specific biological pathways makes it a valuable tool for understanding disease mechanisms and identifying new drug targets. A recent review article in the Nature Reviews Drug Discovery highlighted the importance of such chemical probes in accelerating drug discovery processes.

Conclusion

N-((2R,3S,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide (CAS No. 7772-94-3) is a multifaceted compound with significant potential in various areas of medicinal chemistry and pharmaceutical research. Its unique chemical structure and biological activities make it an attractive candidate for further investigation and development. As research continues to uncover new insights into its mechanisms of action and therapeutic applications, this compound is poised to play a crucial role in advancing our understanding and treatment of various diseases.

• 14131-60-3(b-D-Galactopyranose,2-(acetylamino)-2-deoxy-)
• 1136-42-1(Galactopyranose,2-(acetylamino)-2-deoxy-)
• 157668-96-7(N-1,2-13C2Acetyl-D-glucosamine)
• 14215-68-0(N-Acetyl-D-galactosamine)
• 7512-17-6(N-Acetyl-D-Glucosamine)
• 10036-64-3(N-Acetyl-a-D-glucosamine)
• 14131-68-1(N-(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-ylacetamide)
• 14131-64-7(N-(2S,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-ylacetamide)
• 125304-10-1(Poly(oxy-1,2-ethanediyl),a-(carboxymethyl)-w-(dinonylphenoxy)-, branched)
• 1398-61-4(Chitin, Practical Grade)