129728-92-3

Usage

Uses

Used in Medicinal Chemistry:
2-Acetamido-2,4-dideoxy-4-fluoro-D-galactopyranose is used as a key component in the development of antiviral and antifungal drugs due to its unique structure and properties. Its ability to interact with specific biological targets makes it a promising candidate for the treatment of various viral and fungal infections.
Used in Carbohydrate Metabolism Research:
2-ACETAMIDO-2,4-DIDEOXY-4-FLUORO-D-GALACTOPYRANOSE is used as a valuable tool in understanding the biochemical processes of carbohydrate metabolism. Its unique structure allows researchers to study the interactions between carbohydrates and enzymes, providing insights into the mechanisms of carbohydrate metabolism and the development of new therapeutic agents.
Used in Vaccine Development:
2-Acetamido-2,4-dideoxy-4-fluoro-D-galactopyranose has potential applications in the development of carbohydrate-based vaccines for various infectious diseases. Its unique structure can be used to design vaccines that target specific pathogens, potentially leading to more effective and targeted treatments for infectious diseases.

Upstream product

• 115973-74-5 benzyl 2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside 
• 82827-77-8 Benzyl-2-acetamido-2-desoxy-3,6-di-O-dibenzoyl-α-D-glucopyranosid 
• 141019-70-7 Benzyl-2-acetamido-3,6-di-O-benzoyl-2-desoxy-α-D-galactopyranosid 
• 38416-14-7 benzyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-mesyl-α-D-glucopyranoside 
• 55287-49-5 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 14146-28-2 benzyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-trityl-α-D-glucopyranoside 
• 120596-16-9 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(methylsulfonyl)-α-D-glucopyranoside 
• 174771-87-0 2-acetamido-2-deoxy-1,3-di-O-acetyl-6-O-(triphenylmethyl)-α-D-galactopyranose 
• 1375729-81-9 2-acetamido-2,4-dideoxy-1,3-di-O-acetyl-4-fluoro-6-O-(triphenylmethyl)-α-D-galactopyranose 
• 72-87-7 N-acetyl-D-galactosamine 
• 50605-19-1 2-acetamido-2-deoxy-1,3-di-O-acetyl-α-D-galactopyranose 
• 120596-17-0 benzyl 2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-4-fluoro-α-D-galactopyranoside 
• 104684-58-4 allyl 2-acetamido-3-O-acetyl-2-deoxy-α-D-galactopyranoside 
• 84730-35-8 allyl 2-acetamido-3,6-di-O-acetyl-2-deoxy-α-D-galactopyranoside 

Downstream Products

• 74024-19-4 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-α-D-glucopyranose 
• 116049-57-1 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-α,β-D-glucopyranose 
• 115973-78-9 benzyl 6-O-[2-acetamido-2,4-dideoxy-4-fluoro-β-D-glucopyranosyl]-2-acetamido-2-deoxy-α-D-galactopyranoside 
• 115973-77-8 benzyl 2-acetamido-6-O-(2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-4-fluoro-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-α-D-galactopyranoside 
• 120596-18-1 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-4-fluoro-α-D-galactopyranosyl dibenzyl phosphate 
• 120596-20-5 dilithium uridine 5'-(2-acetamido-2,4-dideoxy-4-fluoro-α-D-galactopyranosyl)diphosphate 

Relevant academic research and scientific papers

Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

Multiple fluorination of glycostructures has emerged as an attractive way of modulating their protein affinity, metabolic stability, and lipophilicity. Here we described the synthesis of a series of mono-, di- and trifluorinated N-acetyl-D-glucosamine and D-galactosamine analogs. The key intermediates are the corresponding multiply fluorinated glucosazide and galactosazide thioglycosides prepared from deoxyfluorinated 1,6-anhydro-2-azido-β-D-hexopyranose precursors by ring-opening reaction with phenyl trimethylsilyl sulfide. Nucleophilic deoxyfluorination at C4 and C6 by reaction with DAST, thioglycoside hydrolysis and azide/acetamide transformation completed the synthesis.

Glycomics for drug discovery: Metabolic perturbation in androgen-independent prostate cancer cells induced by unnatural hexosamine mimics

Inhibited: N-acetylglucosamine (GlcNAc) derivatives with a fluorine atom at the C4 position (2-4) were synthesized, and their ability to inhibit cancer-cell growth was investigated. The administration of these 4F-GlcNAc derivatives to cells led to the unn

Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose and their effects on cellular glycosaminoglycan biosynthesis

4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose (16) exhibited a reduction of [3H]GlcN and [35S]SO4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-galactopyranose (31) exhibited a reduction of [3H]GlcN and [35S]SO4 incorporation to 1 and 9%, respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [14C]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM. Copyright (C) 2000 Elsevier Science Ltd.

Fluorinated carbohydrates as potential plasma membrane modifiers. Synthesis of 4- and 6-fluoro derivatives of 2-acetamido-2-deoxy-D-hexopyranoses.

2-Amino-2,4-dideoxy-4-fluoro- and 2-amino-2,4,6-trideoxy-4, 6-difluoro-D-galactose, and 2-amino-2,4-dideoxy-4-fluoro- and 2-amino-4-deoxy-4, 4-difluoro-D-xylo-hexose were synthesized, as potential modifiers of tumor cell-surface glyco-conjugate, from benz

Synthesis of uridine 5'-(2-acetamido-2,4-dideoxy-4-fluoro-alpha-D-galactopyranosyl) diphosphate and uridine 5'-(2-acetamido-2,6-dideoxy-6-fluoro-alpha-D-glucopyranosyl) diphosphate.

Benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside was converted into its 4-O-(methylsulfonyl) derivative (2) by treatment with methanesulfonyl chloride in pyridine. Displacement of the methylsulfonyloxy group of 2 with fluoride ion afforded benzyl 2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-4-fluoro-alpha-D-galactopyranosi de, which on hydrogenolysis, followed by acetylation, furnished 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-galactopyranose. Treatment of this and of 2-acetamido-1,3,4-tri-O-acetyl-2,6-dideoxy-6-fluoro-D-glucopyranose with trimethylsilyl trifluoromethanesulfonate in 1,2-dichloroethane at approximately 50 degrees afforded the 4-deoxy-4-fluoro- or the 6-deoxy-6-fluoro-oxazolines (5) and (11), respectively. Reaction of 5 and 11 with dibenzyl phosphate in 1,2-dichloroethane produced the alpha-linked dibenzyl phosphate derivatives 6 and 12, respectively. Catalytic hydrogenation of 6 provided 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-4-fluoro-alpha-D-galactopyranosy l phosphate (7), and that of 12 gave 2-acetamido-3,4-di-O-acetyl-2,6-dideoxy-6-fluoro-alpha-D-glucopyranosyl phosphate (13). Coupling of 7 and 13 with uridine 5'-monophosphomorpholidate in dry pyridine at approximately 37 degrees, followed by O-deacetylation, furnished the title compounds, respectively, isolated and characterized as their respective dilithium salts.

Synthesis of D-galactosamine derivatives and binding studies using isolated rat hepatocytes.

Derivatives of glycosides of D-galactosamine were prepared in order to study further the binding requirement of the Gal/GalNAc receptor in mammalian hepatocytes. These structures included N-propanoyl, N-benzoyl, and N,N-phthaloyl derivatives of 2-hydroxye