87326-62-3

Upstream product

• 98-88-4 benzoyl chloride 
• 67546-20-7 1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 214117-33-6 1,6-anhydro-2-azido-3-O-benzoyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranose 
• 55682-47-8 1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose 
• 55682-48-9 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose 
• 33208-47-8 4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose 

Relevant academic research and scientific papers

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.

Synthesis of S-Linked Thiooligosaccharide Analogues of Nodulation Factors. 2.1 Synthesis of an Intermediate Thiotrisaccharide

An S-linked thiotrisaccharide analogue of chitin that carries different N-protecting groups at the reducing and nonreducing end glucosamine residues was prepared as an intermediate for the synthesis of thioanalogues of nodulation factors. 1,6-Anhydro-2-azido-3-O-benzoyl-2-deoxy-β-D-glucopyranose (3) was prepared either through the nucleophilic displacement of the 4-triflate galacto analogue 1 with potassium chloroacetate or via the selective acylation of the analogous gluco diol 4. Condensation of 3 with the N-phthalimido trichloroacetimidate 9 led to the disaccharide 10, which was converted in four steps to the glucosyl bromide 15. Nucleophilic displacement of the anomeric bromide by a 4-thiolate derivative of glucosamine (16) bearing a trichloroethoxycarbamate at C-2 was performed in anhydrous oxygen-free THF and led to the desired thiotrisaccharide precursor of thioanalogues of nodulation factors. Alternatively, the disaccharide 10 was prepared by regioselective glycosylation of the 1,6-anhydro diol 4 followed by benzoylation of the remaining free hydroxyl group.