[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-prop-2-ynoxyoxan-2-yl]methyl acetate

[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-prop-2-ynoxyoxan-2-yl]methyl acetate

[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-prop-2-ynoxyoxan-2-yl]methyl acetate (CAS No. 869003-30-5) is a specialized compound that plays a significant role in carbohydrate chemistry and synthetic organic chemistry. This compound features a unique structure characterized by multiple functional groups that enhance its reactivity and applicability in various biochemical processes.

Chemical Properties

• CAS Number: 869003-30-5
• MDL Number: MFCD19981017
• EINECS: Not available
• Molecular Formula: C17H23NO9
• Molecular Weight: 385.37 g/mol
• Boiling Point: Not specified
• Melting Point: Not specified
• Appearance: Typically appears as a white to off-white solid or powder

Structure and Composition

The structure of [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-prop-2-ynoxyoxan-2-yl]methyl acetate consists of several key components:

1. Acetamido Group: The acetamido functional group at position 5 contributes to the compound’s stability and solubility while providing a reactive site for further chemical modifications.
2. Diacetyloxy Groups: The presence of two acetyl groups at positions 3 and 4 protects the hydroxyl groups, enhancing the compound’s stability and facilitating selective reactions during synthesis.
3. Propynyl Ether: The propynyl ether group at position 6 adds to the compound’s structural complexity and potential reactivity, allowing for diverse chemical transformations.
4. Sugar Backbone: The oxan structure provides a carbohydrate framework that is essential for biological recognition processes.

Applications

[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-prop-2-ynoxyoxan-2-yl]methyl acetate 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. Synthetic Chemistry: The unique functional groups make it a valuable intermediate in the synthesis of more complex carbohydrate derivatives and glycoconjugates.

Pharmaceutical Development

1. Drug Design: Its 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 various bioactive compounds and pharmaceuticals.

Safety and Handling

While specific safety data for [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-prop-2-ynoxyoxan-2-yl]methyl acetate 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, [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-prop-2-ynoxyoxan-2-yl]methyl acetate (CAS No. 869003-30-5) is an important reagent in carbohydrate chemistry for studying glycosylation processes and facilitating synthetic 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://molekula.com/catalog/110-30-5/89967033-nn-ethylenebisstearamide?locale=en
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