1,2,3,4,6-Penta-O-trimethylsilyl-D-glucopyranose

1,2,3,4,6-Penta-O-trimethylsilyl-D-glucopyranose

1,2,3,4,6-Penta-O-trimethylsilyl-D-glucopyranose is a highly modified derivative of D-glucose that serves as a crucial intermediate in carbohydrate chemistry. This compound is characterized by its five trimethylsilyl (TMS) groups, which protect the hydroxyl functionalities of glucose, facilitating selective reactions and enhancing stability.

Chemical Identity

• CAS Number: 19126-99-9
• MDL Number: MFCD09841154
• Catalog Number: A1251138
• Molecular Formula: C₂₁H₅₂O₆Si₅
• Molecular Weight: 541.06 g/mol

Physical Properties

• Boiling Point: Approximately 432.1 ± 45.0 °C
• Melting Point: Not explicitly listed but typically stable under standard laboratory conditions.
• Density: 0.94 ± 0.1 g/cm³
• Appearance: Typically a white to off-white powder or crystalline solid.
• Storage Conditions: Store in a cool, dry place away from moisture for long-term stability.

Structural Features

This compound features:

• A D-glucopyranose backbone with five trimethylsilyl groups attached at the 1, 2, 3, 4, and 6 positions.
• The TMS groups serve as protective groups that prevent unwanted reactions at the hydroxyl sites during synthesis.
• The β-anomeric configuration is retained, which is critical for its reactivity in glycosylation processes.

Applications

1,2,3,4,6-Penta-O-trimethylsilyl-D-glucopyranose is utilized in various fields:

• Carbohydrate Synthesis: Acts as a glycosyl donor for synthesizing complex carbohydrates and glycoconjugates.
• Glycosylation Reactions: Employed for the assembly of oligosaccharides and other carbohydrate derivatives.
• Analytical Techniques: Used in gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) spectroscopy for structural elucidation and characterization of carbohydrates and glycoconjugates.
• Biochemical Research: Facilitates studies involving carbohydrate-protein interactions and the development of carbohydrate-based ligands.

Safety and Handling

• Hazard Statements: Generally considered safe when handled properly; however, standard laboratory precautions should be observed.
• Storage Conditions: Store at room temperature in a tightly sealed container to prevent moisture absorption.

Regulatory Information

This compound is expected to comply with TSCA regulations but should be verified for specific handling requirements based on local regulations.

1,2,3,4,6-Penta-O-trimethylsilyl-D-glucopyranose is commercially available for research purposes and plays a vital role in advancing carbohydrate chemistry and related fields. Its unique structure allows for versatile applications in both synthetic and analytical chemistry.

Citations:

1. https://www.scbt.com/p/1-2-3-4-6-penta-trimethylsilyl-glucopyranose
2. https://pubchem.ncbi.nlm.nih.gov/compound/13587621
3. https://pubchem.ncbi.nlm.nih.gov/compound/11038830
4. https://cymitquimica.com/products/3D-MP06937/19126-99-9/12346-penta-o-trimethylsilyl-d-glucopyranose/
5. https://www.chemeo.com/cid/61-932-9/%C2%ABalpha%C2%BB-D-Glucopyranose,%201,2,3,4,6-pentakis-O-(trimethylsilyl)-
6. https://www.chemeo.com/cid/77-109-6/beta-D-Glucopyranose-1-2-3-4-6-pentakis-O-trimethylsilyl
7. https://www.biosynth.com/p/MP06937/19126-99-9-12346-penta-o-trimethylsilyl-d-glucop
8. https://www.bocsci.com/product/1-2-3-4-6-penta-o-trimethylsilyl-d-cas-19126-99-9-61.html