3947-62-4 | 2,3,4,6-Tetra-O-acetyl-beta-D-glucose

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$90.00	$63.00
1g	97%	in stock	$203.00	$142.00
5g	97%	in stock	$822.00	$575.00

Description

• Catalog Number: AD38173
• Chemical Name: 2,3,4,6-Tetra-O-acetyl-beta-D-glucose
• CAS Number: 3947-62-4
• Molecular Formula: C14H20O10
• Molecular Weight: 348.3026
• MDL Number: MFCD00270571
• SMILES: CC(=O)OC[C@H]1O[C@@H](O)[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C

Computed Properties

• Complexity: 502
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 5
• Heavy Atom Count: 24
• Hydrogen Bond Acceptor Count: 10
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 9
• XLogP3: 0.1

Upstream Synthesis Route

2,3,4,6-Tetra-O-acetyl-β-D-glucose, commonly known as Tetraacetylglucose, is a versatile compound utilized in various chemical synthesis applications. This compound serves as a key building block in organic chemistry, particularly in the modification of carbohydrates and glycosides. Its specific structure containing multiple acetyl groups imparts unique reactivity, making it an essential component in the preparation of complex organic molecules.In chemical synthesis, 2,3,4,6-Tetra-O-acetyl-β-D-glucose is often employed as a protecting group for the hydroxyl (OH) functional groups present in carbohydrates. By acetylating these hydroxyl groups, the reactivity of the respective positions is masked, allowing selective manipulation of other regions of the molecule without interference. Subsequent deprotection of the acetyl groups can then be achieved under controlled conditions, enabling the targeted synthesis of desired carbohydrate derivatives and glycosides.Furthermore, Tetraacetylglucose is also utilized in the preparation of various glycosidic linkages through glycosylation reactions. By utilizing the acetylated glucose derivative as a glycosyl donor or acceptor, chemists can facilitate the formation of glycosidic bonds between different carbohydrate molecules or aglycones. This process is essential in the synthesis of natural products, pharmaceuticals, and other biologically active compounds that contain carbohydrate moieties.Overall, the versatile nature of 2,3,4,6-Tetra-O-acetyl-β-D-glucose makes it a valuable tool in chemical synthesis, enabling precise modification and manipulation of carbohydrates for the generation of diverse organic compounds with targeted properties and functions.