2,3,4,6-Tetra-O-benzyl-D-glucopyranose
[CAS# 4132-28-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyran compound
• Name: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
• Synonyms: (3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.66
• CAS Registry Number: 4132-28-9
• EC Number: 609-908-7
• SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H](C(O2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 151-156 °C (Expl.)
• Index of Refraction: 1.619, Calc.^*
• Boiling Point: 672.4±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 360.4±31.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2,3,4,6-Tetra-O-benzyl-D-glucopyranose is a glucopyranose derivative where all the hydroxyl groups on the glucose molecule are protected with benzyl groups. This compound is an important intermediate in carbohydrate chemistry, widely used for synthesizing other complex carbohydrate derivatives. The benzyl groups act as protecting groups, preventing unwanted reactions during further chemical manipulations and enabling selective functionalization of the glucose molecule.

The discovery of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose can be traced back to the development of protecting group strategies in carbohydrate chemistry. The protection of hydroxyl groups using benzyl groups is a well-established method that allows for the selective derivatization of other positions on the glucose molecule. This strategy has proven essential in the synthesis of oligosaccharides, glycoconjugates, and other carbohydrate-based compounds, which have significant applications in both pharmaceuticals and materials science.

The synthesis of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose typically involves the selective benzylation of D-glucopyranose in the presence of a base, such as potassium carbonate or sodium hydride. The reaction is carried out in an appropriate solvent, often anhydrous dimethylformamide (DMF), which helps facilitate the formation of the benzyl ether groups. This reaction selectively protects the hydroxyl groups at the 2, 3, 4, and 6 positions, leaving the glucose molecule in its protected form. Once the desired synthesis is complete, the benzyl groups can be selectively removed in subsequent steps to expose the hydroxyl groups for further reactions, such as glycosylation or coupling with other biomolecules.

The applications of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose are vast and varied. In the field of carbohydrate chemistry, it serves as a valuable intermediate for the synthesis of complex oligosaccharides, which are important for studying glycobiology, the interaction between carbohydrates and proteins. These compounds are often used in drug discovery, as carbohydrates play a critical role in cellular recognition and signaling processes. Moreover, 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is frequently employed in the development of glycoproteins, which are used as therapeutic agents for diseases like cancer and viral infections.

In the realm of materials science, 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is used to modify and functionalize surfaces and polymers. Its ability to introduce hydroxyl groups at specific positions on the glucose ring allows for the design of carbohydrate-based materials with tailored properties. These materials are often employed in creating biocompatible surfaces, sensors, and bioactive materials for medical applications. Furthermore, the versatility of this compound in terms of its protection and deprotection chemistry makes it an essential tool for developing new synthetic routes and materials.

In conclusion, 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is a crucial intermediate in carbohydrate chemistry, enabling the synthesis of complex sugar derivatives for use in a wide range of applications. Its ability to serve as a precursor for oligosaccharides and glycoconjugates underscores its importance in pharmaceutical and materials science. With continued research and development, 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is likely to play an even larger role in advancing the understanding of carbohydrate-related processes and developing new therapeutic materials.

References

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DOI: 10.1055/s-2008-1067257

2002. Potential bile acid metabolites. 24. An efficient synthesis of carboxyl-linked glucosides and their chemical properties. Lipids, 37(1).
DOI: 10.1007/s11745-002-0869-3