57632-01-6

Usage

Chemical compound

A substance with a specific molecular structure resulting from a chemical reaction.

Derivative of galactose

A type of sugar, which is a monosaccharide and a component of lactose.

Contains two benzoyl groups

These are functional groups derived from benzoic acid, which are attached to the sugar molecule.

Complex molecular structure

The compound has a unique arrangement of atoms and bonds that give it specific properties.

Applications in carbohydrate chemistry

It can be used to study and manipulate carbohydrate molecules, which are essential components of many biological processes.

Glycosylation reactions

The compound can be used in reactions that involve the formation or modification of glycosidic bonds, which are important in the synthesis of complex carbohydrates.

Building block for complex sugar molecules

It can be used as a starting material for the synthesis of more complex sugar molecules, which have various applications in biochemistry and pharmaceuticals.

Reagent in organic chemistry

It can be used as a reactant or catalyst in various organic chemical reactions.

Valuable tool for studying carbohydrate molecules

Its unique structure and properties make it useful for understanding the behavior and function of carbohydrates in biological systems.

Potential implications in drug development and biochemistry

The compound's properties and applications may contribute to the development of new drugs and the study of biological processes involving carbohydrates.

Upstream product

• 23567-05-7 1,6-Anhydro-2,3,4-tri-O-benzoyl-β-D-glucopyranose 
• 98-88-4 benzoyl chloride 
• 498-07-7 levoglucosan 

Downstream Products

• 137334-32-8 C₃₄H₃₆O₁₆ 
• 88142-90-9 1,6-anhydro-2,4-O-dibenzoyl-3-O-trimethylsilyl-β-D-glucopyranose 

Relevant academic research and scientific papers

Synthesis of unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose via stereoselective photobromination of 2,3-isopropylidene-4-benzoyl-1,6-anhydro-β-D-mannopyranose

Stereoselective photobromination of 1,6-anhydro-β-D-glucopyranose derivatives occurs at exo-H6. However, photobromination of 4-benzoyl-2,3-isopropylidene-1,6-anhydro-β-D-mannopyranose 6 produced unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose 7. The mechanism of stereoselective oxidation at C-3 could be attributed to the facile radical proton abstraction at C-3, followed by the subsequent bromination of the isopropylidene group, which was subsequently eliminated during the aqueous workup. Thus, the aim of this article is to identify the molecular structure of the unstable compound 7.

Synthesis of oligosaccharides related to the HNK-1 antigen. 5. Synthesis of a sulfo-mimetic of the HNK-1 antigenic trisaccharide

2-Aminoethyl 3,6-di-O-sulfo-β-D-glucopyranosyl-(1→3)-β-D- galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside, which is the sulfo-mimetic of the antigenic trisaccharide HNK-1, and the corresponding monosulfates, viz., 2-aminoethyl 3-O-sulfo-and 2-aminoethyl 6-O-sulfo-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→ 4)-2-acetamido-2-deoxy-β-D-glucopyranosides, were synthesized. 2-Azidoethyl 2,4-di-O-benzoyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-benzoyl-β- D-galactopyranosyl-(1→ 4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D- glucopyranoside served as the common precursor for the sulfated trisaccharides. This compound was synthesized according to the [2+1] pattern from monosaccharidic precursors: 3,6-di-O-acetyl-2,4-di-O-benzoyl-D-glucopyranosyl trichloroacetimidate, allyl 2-O-benzoyl-4,6-O-benzylidene-β-D- galactopyranoside, and 2-azidoethyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β- D-glucopyranoside. The structures of the glycosyl donors and glycosylation conditions were optimized for the efficient synthesis of the glucosyl-β-(1→3)-galactose disaccharide block and its subsequent transformation into the target trisaccharide sequence.

PARTIAL HYDROLYSIS OF ACYL 1,6-ANHYDRO-β-D-GLUCOPYRANOSE

Partial hydrolysis of per-O-acetyl- and per-O-benzoyl derivatives of 1,6-anhydro-β-D-glucopyranose with methanolic hydrogen chloride and hydrazine hydrate was investigated.The acyl group at C(3) is of substantial influence on the course of hydrolysis.The esterified hydroxyl group at C(3) was found to be most stable on acid hydrolysis with methanolic hydrogen chloride when compared with that at C(2), or C(4); on the other hand, this ester group is the most labile upon hydrolysis with hydrazine hydrate.Selectivity of the respective ester groups towardshydrolysis made it possible to prepare all variations of acetyl and benzoyl derivatives of 1,6-anhydro-β-D-glucopyranose.