33639-93-9

Upstream product

• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 121523-91-9 1-O-acetyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranose 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose 
• 105376-04-3 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 492-61-5 β-D-glucose 

Downstream Products

• 15355-08-5 N-benzoyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylamine 
• 1158796-36-1 1-(2,3,4,6-tetra-O-benzoyl-β-D-mannosyl)-4-tert-butoxycarbonyl-1H-1,2,3-triazole 
• 1158796-22-5 1-(2,3,4,6-tetra-O-benzoyl-β-D-glucosyl)-1H-benzo[d][1,2,3]triazole 
• 1158796-33-8 1-(2,3,4,6-tetra-O-benzoyl-β-D-glucosyl)-4-phenyl-1H-1,2,3-triazole 
• 1158796-35-0 1-(2,3,4,6-tetra-O-benzoyl-β-D-glucosyl)-4-methoxycarbonyl-1H-1,2,3-triazole 
• 1158796-32-7 3,4-bis-(methoxycarbonyl)-1-(2,3,4,6-tetra-O-benzoyl-β-D-glucosyl)-1H-1,2,3-triazole 

Relevant academic research and scientific papers

1-Fluoropyridinium triflates: Versatile reagents for transformation of thioglycoside into O-glycoside, glycosyl azide and sulfoxide

1-Fluoropyridinium triflates are versatile reagents to transform thioglycoside into O-glycoside, glycosyl azide and sulfoxide. The electronic nature of the substituents on the pyridine ring can control their ability to activate thioglycosides.

Synthesis, molecular docking analysis and biological evaluations of saccharide-modified thiadiazole sulfonamide derivatives

A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors.

AuBr3-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr3 in good to excellent yields. The method is applicable to a wide range of easily accessible per-Oacetylated and per-O-benzoylated sugars. While reaction with per-O-acetylated and per-O-benzoylated monosaccharides was complete within 1-3 h at room temperature, the per-O-benzoylated disaccharides needed 2-3 h of heating at 55°C.

Stable Alkynyl Glycosyl Carbonates: Catalytic Anomeric Activation and Synthesis of a Tridecasaccharide Reminiscent of Mycobacterium tuberculosis Cell Wall Lipoarabinomannan

Oligosaccharide synthesis is still a challenging task despite the advent of modern glycosidation techniques. Herein, alkynyl glycosyl carbonates are shown to be stable glycosyl donors that can be activated catalytically by gold and silver salts at 25 °C in just 15 min to produce glycosides in excellent yields. Benzoyl glycosyl carbonate donors are solid compounds with a long shelf life. This operationally simple protocol was found to be highly efficient for the synthesis of nucleosides, amino acids, and phenolic and azido glycoconjugates. Repeated use of the carbonate glycosidation method enabled the highly convergent synthesis of tridecaarabinomannan in a rapid manner.

Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates

Numerous deoxy-azido sugars 3 were prepared by the reaction of tosyl/bromo sugars with NaN3 in dry DMF under heating condition. The 1,3-dipolar cycloaddition of deoxy-azido sugars 3 with ethisterone 4 to afford regioselective triazole-linked ethisterone glycoconjugates 5 was investigated in the presence of CuI and DIPEA in dichloromethane or CuSO4· 5H2O and sodium ascorbate in aqueous medium. All the developed compounds were characterized by spectroscopic analysis (IR, 1H & 13C NMR, and MS spectra). Structure of triazolyl ethisterone glycoconjugate 5a has been further confirmed by its Single Crystal X-ray analysis.

High-Yielding Catalytic Synthesis of Glycosyl Azides from Peracylated Sugars

In the presence of a catalyst generated from SnCl4 and AgClO4, or Yb(OTf)3, various glycosyl azides are synthesized in high yields with complete stereoselectivities from peracylated sugars and trimethylsilyl azide by choosing a suitable solvent such as dichloromethane or nitromethane.

Tetramethylguanidinium azide as a new reagent for the stereoselective synthesis of glycosyl azides

Tetramethylguanidium azide was used in the quantitative conversion of glycosyl halides 1 - 6 to the corresponding glycosyl azides 7 - 12. The stereoselective reactions occurred with complete inversion at the anomeric centers.