N-[(2R,3R,4R,5S,6R)-2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

N-[(2R,3R,4R,5S,6R)-2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

N-[(2R,3R,4R,5S,6R)-2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide (CAS No. 86520-54-9) is a specialized azido sugar derivative that is significant in biochemical research and synthetic chemistry. This compound is characterized by its complex structure, which includes multiple functional groups that enhance its reactivity and utility in various applications.

Chemical Properties

• CAS Number: 86520-54-9
• MDL Number: MFCD21363174
• EINECS: Not available
• Molecular Formula: C14H26N4O8
• Molecular Weight: 378.38 g/mol
• Boiling Point: Not specified
• Melting Point: Not specified
• Appearance: Typically appears as a white to off-white powder or solid

Structure and Composition

The structure of N-[(2R,3R,4R,5S,6R)-2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide features several key components:

1. Azido Group: The presence of the azido functional group (-N₃) allows for click chemistry applications, facilitating the conjugation with other biomolecules.
2. Acetamide Moiety: The acetamide group enhances the compound’s stability and solubility while providing a reactive site for further chemical modifications.
3. Hydroxyl Groups: Multiple hydroxyl groups at positions 4 and 5 contribute to the compound’s high polarity and ability to form hydrogen bonds, which are crucial for biological interactions.
4. Ethylene Glycol Linkers: The inclusion of ethylene glycol units increases solubility and can improve the bioavailability of the compound in biological systems.

Applications

N-[(2R,3R,4R,5S,6R)-2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide is utilized in several applications:

Biochemical Research

1. Glycosylation Studies: This compound can serve as a substrate for glycosyltransferases, enabling researchers to investigate glycosylation pathways and enzyme kinetics.
2. Click Chemistry: The azido group allows for efficient labeling and conjugation with various biomolecules including proteins and nucleic acids.

Pharmaceutical Development

1. Drug Design: Its unique structural features make it a candidate for developing glycosylated drugs that require specific targeting mechanisms or enhanced bioactivity.

Chemical Synthesis

1. Intermediate in Synthesis: It can be used as an intermediate in the synthesis of more complex carbohydrate derivatives and glycoconjugates.

Safety and Handling

While specific safety data for N-[(2R,3R,4R,5S,6R)-2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide are not extensively documented, standard laboratory safety practices should be followed:

1. Personal Protective Equipment (PPE): Use gloves, goggles, and lab coats when handling this compound to avoid skin or eye contact.
2. Ventilation: Work in a well-ventilated area or fume hood to minimize exposure to vapors or dust.
3. Storage Conditions: Store the compound at temperatures between 2 to 8 °C to maintain stability.
4. Disposal Guidelines: Dispose of waste according to local regulations regarding hazardous materials.

Summary

In summary, N-[(2R,3R,4R,5S,6R)-2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide (CAS No. 86520-54-9) is an important reagent in biochemical research for studying glycosylation processes and facilitating click chemistry reactions. Its unique structural features enable its use in synthesizing glycosylated compounds with potential applications in drug development and enzymatic assays.

Citations:

1. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4199395.htm
2. https://pubchem.ncbi.nlm.nih.gov/compound/Trisodium-phosphate
3. https://en.wikipedia.org/wiki/Hexane
4. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7132531.htm
5. https://www.sigmaaldrich.com/BR/en/search/86520-54-9?focus=products&page=1&perpage=30&sort=relevance&term=86520-54-9&type=cas_number
6. https://www.merckmillipore.com/NO/en/product/2-Fluoroaniline,MDA_CHEM-820565