1309463-38-4

Basic information

• Product Name: 4-Deoxy-4-fluoro-1,2,3,6-tetra-O-benzoyl-α-D-mannose
• Synonyms: 4-Deoxy-4-fluoro-1,2,3,6-tetra-O-benzoyl-α-D-mannose
• CAS NO: 1309463-38-4
• Molecular Formula: C34H27FO9
• Molecular Weight: 598.5711832
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 1309463-38-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane
• CAS DataBase Reference: 4-Deoxy-4-fluoro-1,2,3,6-tetra-O-benzoyl-α-D-mannose(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Deoxy-4-fluoro-1,2,3,6-tetra-O-benzoyl-α-D-mannose(1309463-38-4)
• EPA Substance Registry System: 4-Deoxy-4-fluoro-1,2,3,6-tetra-O-benzoyl-α-D-mannose(1309463-38-4)

Safety Data

• Hazardous Substances Data: 1309463-38-4(Hazardous Substances Data)

Usage

Description

4-Deoxy-4-fluoro-1,2,3,6-tetra-O-benzoyl-α-D-mannose is a complex organic compound characterized by the absence of a hydroxyl group at the fourth carbon and the presence of a fluorine atom at the same position. It features a mannose sugar core with four benzoyl groups attached to the first, second, third, and sixth carbons, which significantly influences its chemical properties and reactivity. This white foam substance is a valuable intermediate in organic synthesis, particularly for the preparation of various pharmaceuticals and bioactive molecules.

Uses

Used in Organic Synthesis:
4-Deoxy-4-fluoro-1,2,3,6-tetra-O-benzoyl-α-D-mannose is used as a synthetic intermediate for the preparation of complex organic molecules. Its unique structure allows for selective reactions and modifications, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Deoxy-4-fluoro-1,2,3,6-tetra-O-benzoyl-α-D-mannose is used as a key component in the development of novel drug candidates. Its unique structural features can be exploited to design and synthesize new molecules with potential therapeutic applications, including the treatment of various diseases and disorders.
Used in Research and Development:
4-Deoxy-4-fluoro-1,2,3,6-tetra-O-benzoyl-α-D-mannose is also utilized in research and development settings to explore its chemical properties and reactivity. Scientists and chemists use this compound to study reaction mechanisms, investigate the influence of structural modifications on biological activity, and develop new synthetic methodologies.
Used in Bioactive Molecule Synthesis:
Due to its unique structure and reactivity, 4-Deoxy-4-fluoro-1,2,3,6-tetra-O-benzoyl-α-D-mannose is employed in the synthesis of bioactive molecules with potential applications in various fields, such as medicine, agriculture, and materials science. Its ability to be selectively modified and functionalized makes it an attractive candidate for the development of new bioactive compounds with improved properties and efficacy.

Upstream product

• 1228019-06-4 1,2,3,6-tetra-O-benzoyl-β-D-galactopyranose 
• 59-23-4 D-Galactose 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 1606980-47-5 C₃₄H₂₈O₁₀ 
• 1606980-55-5 C₃₄H₂₇N₃O₉ 
• 530-26-7 D-Mannose 
• 1344035-31-9 1,2,3,6-tetra-O-benzoyl-4-(1,1,1-trifluoromethanesulfonyl)-β-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 1228019-10-0 C₃₅H₂₇F₃O₁₂S 
• 114718-46-6 1,2,3,6-tetra-O-benzoyl-α-D-galactopyranose 

Relevant articles and documents

Chemoenzymatic synthesis of sialosides containing C7-modified sialic acids and their application in sialidase substrate specificity studies

Modifications at the glycerol side chain of sialic acid in sialosides modulate their recognition by sialic acid-binding proteins and sialidases. However, limited work has been focused on the synthesis and functional studies of sialosides with C7-modified

Process development of selectively benzoylated and fluorinated glycosyl donors

Route selection, process development and large-scale preparation of selectively benzoylated and fluorinated d-glucopyranoses, required as glycosyl donors for the synthesis of the SGLT inhibitor SAR7226, are discussed.

Elucidation of the mechanism of polysaccharide cleavage by chondroitin AC lyase from Flavobacterium heparinum

Chondroitin AC lyase from Flavobacterium heparinum degrades chondroitin sulfate glycosaminoglycans via an elimination mechanism resulting in disaccharides or oligosaccharides with Δ4,5-unsaturated uronic acid residues at their nonreducing end. Mechanistic details concerning the ordering of the bond-breaking and -forming steps of this enzymatic reaction are nonexistent, mainly due to the inhomogeneous nature of the polymeric substrates. The creation of a new class of synthetic substrates for this enzyme has allowed the measurement of defined and reproducible kcat and Km values and has expanded the range of mechanistic studies that can be performed. The primary deuterium kinetic isotope effect upon kcat/Km for the abstraction of the proton α to the carboxylic acid was measured to be 1.67 ± 0.07, showing that deprotonation occurs in a rate-limiting step. Using substrates with leaving groups of differing reactivity, a flat linear free energy relationship was produced, indicating that the C4-O4 bond is not broken in a rate-determining step. Taken together, these results strongly suggest a stepwise mechanism. Consistent with this was the measurement of a secondary deuterium kinetic isotope effect upon kcat/Km of 1.01 ± 0.03 on a 4-{2H}-substrate, indicating that no sp2 character is developed at C4 during the rate-limiting step, thereby ruling out a concerted syn-elimination.