74024-19-4

Upstream product

• 129728-87-6 2-acetamido-2,4-dideoxy-4-fluoro-α,β-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 75869-83-9 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranoside 
• 115973-74-5 benzyl 2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-4-fluoro-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 
• 129728-93-4 benzyl 2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranoside 
• 14146-28-2 benzyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-trityl-α-D-glucopyranoside 
• 55287-49-5 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 38416-14-7 benzyl 2-acetamido-3-O-benzyl-2-deoxy-4-O-mesyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

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 and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine

Background: Derivatives of D-glucosamine and D-galactosamine represent an important family of the cell surface glycan components and their fluorinated analogs found use as metabolic inhibitors of complex glycan biosynthesis, or as probes for the study of protein-carbohydrate interactions. This work is focused on the synthesis of acetylated 3-deoxy-3-fluoro, 4-deoxy-4-fluoro and 3,4-dideoxy-3,4-difluoro analogs of D-glucosamine and D-galactosamine via 1,6-anhydrohexopyranose chemistry. Moreover, the cytotoxicity of the target compounds towards selected cancer cells is determined. Results: Introduction of fluorine at C-3 was achieved by the reaction of 1,6-anhydro-2-azido-2-deoxy-4-O-benzyl-β-D-glucopyranose or its 4-fluoro analog with DAST. The retention of configuration in this reaction is discussed. Fluorine at C-4 was installed by the reaction of 1,6:2,3-dianhydro-β-D-talopyranose with DAST, or by fluoridolysis of 1,6:3,4-dianhydro-2-azido-β-D-galactopyranose with KHF2. The amino group was introduced and masked as an azide in the synthesis. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs of acetylated D-galactosamine inhibited proliferation of the human prostate cancer cell line PC-3 more than cisplatin and 5-fluorouracil (IC50 28 ± 3 μM and 54 ± 5 μM, respectively). Conclusion: A complete series of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine is now accessible by 1,6-anhydrohexopyranose chemistry. Intermediate fluorinated 1,6-anhydro-2-azido-hexopyranoses have potential as synthons in oligosaccharide assembly.

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