89539-39-9

Upstream product

• 18685-21-7 methyl 2,3,5,6-tetra-O-benzyl-β-D-galactofuranoside 
• 77874-38-5 Methyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranoside 
• 10257-28-0 D-Galactose 
• 100-39-0 benzyl bromide 
• 139535-13-0 2,3,4,6-tetra-O-benzyl-1-O-(2-nitrobenzenesulfenyl)-α-D-glucopyranose 
• 55902-93-7 methyl 3,5,6-tri-O-benzyl-α,β-D-glucofuranoside 
• 59-23-4 D-Galactose 
• 89539-33-3 benzyl 2,3,5,6-tetra-O-benzyl-α-D-galactofuranoside 
• 35958-64-6 3,5,6-Tri-O-benzyl-D-glucofuranose 
• 201603-51-2 methyl 2,3,5,6-tetra-O-benzylglucofuranoside 
• 28435-60-1 1,4-dideoxy-1,4-imino-5-hydroxy-L-iditol 
• 108-24-7 acetic anhydride 
• 1824-93-7 methyl-β-D-galactofuranoside 

Downstream Products

• 116444-14-5 3,4,6,7-tetra-O-benzyl-1,2-dideoxy-d-galacto-hept-1-enitol 

Relevant academic research and scientific papers

Design, synthesis and bioactivity evaluation of Galf mimics as antitubercular agents

A series of novel Galf mimics has been synthesized and characterized by IR, 1H NMR, 13C NMR, mass spectral and element analysis. All the newly prepared compounds were screened for their antitubercular activities. Bioactivity assays manifested that most of Galf mimics exhibited good antitubercular activities. Especially compound 4d and 4e displayed remarkable antitubercular efficacies, which were comparable to ethambutol.

Compound and preparation method and application thereof

The invention provides a compound shown in the formula I and a preparation method thereof and a method for detecting Gliflozin medicine through high performance liquid chromatography. According to the preparation method, 3,5,6-tribenzyl-D-glucofuranose serves as a raw material, a methylation reaction, a benzyl substitution reaction, demethylating and ketalation are carried out, 3,5,6-tribenzyl-D-glucofuranose and a halide intermediate are subjected to a nucleophilic addition, the material makes contact with triethyl silicane and boron trifluoride diethyl etherate, finally, the material makes contact with ethanethiol and boron trifluoride diethyl etherate, and the target impurity product can be obtained. By means of the method, directional preparation is achieved for synthesis of the target product; the target product provides a reliable impurity reference substance for quality research and impurity quantitative control of industrially-produced Gliflozin series diabetes treatment medicine products. The formula I is shown in the specification.

Synthesis of Unprecedented Sulfonylated Phosphono-exo-Glycals Designed as Inhibitors of the Three Mycobacterial Galactofuranose Processing Enzymes

This study reports a new methodology to synthesize exo-glycals bearing both a sulfone and a phosphonate. This synthetic strategy provides a way to generate exo-glycals displaying two electron-withdrawing groups and was applied to eight different carbohydrates from the furanose and pyranose series. The Z/E configurations of these tetrasubstituted enol ethers could be ascertained using NMR spectroscopic techniques. Deprotection of an exo-glycal followed by an UMP (uridine monophosphate) coupling generated two new UDP (uridine diphosphate)-galactofuranose analogues. These two Z/E isomers were evaluated as inhibitors of UGM, GlfT1, and GlfT2, the three mycobacterial galactofuranose processing enzymes. Molecule 46-(E) is the first characterized inhibitor of GlfT1 reported to date and was also found to efficiently inhibit UGM in a reversible manner. Interestingly, GlfT2 showed a better affinity for the (Z) isomer. The three enzymes studied in the present work are not only interesting because, mechanistically, they are still the topic of intense investigations, but also because they constitute very important targets for the development of novel antimycobacterial agents.

Novel glycolipid TLR2 ligands of the type Pam2Cys-α-Gal: Synthesis and biological properties

A more complete understanding of the mechanism of action of TLR agonists has fueled the investigation of new synthetic immunoadjuvants. In this context, we designed and synthesized glycolipids of the type Pam2Cys-α- Galactose as novel immunoadj

Intramolecular 1,3-dipolar nitrone and nitrile oxide cycloaddition of 2- and 4-O-allyl and propargyl glucose derivatives: A versatile approach to chiral cyclic ether fused isoxazolidines, isoxazolines and isoxazoles

2-O- and 4-O-Allyl and -propargyl glucose and the corresponding oxime derivatives were prepared from readily available glucose dithioacetals. Intramolecular 1,3-dipolar cycloaddition of the N-benzyl and N-methyl nitrones of the above acyclic 2-O-allyl glucose derivatives led to the diastereoselective formation of chiral isoxazolidines incorporating the tetrahydrofuran ring. The EI mass spectra revealed a characteristic cleavage of the C-alkyl group adjacent to the furan oxygen atom. An enantiopure trisubstituted tetrahydrofuran was obtained by the reductive cleavage of the isoxazolidine ring of one of the cycloadducts. In contrast, the nitrile oxide cycloaddition of the 2-O-allyl derivatives afforded diastereomeric mixtures of the corresponding dihydroisoxazolines, the stereochemistry of which was tentatively assigned on the basis of the principle of optical superposition. The exclusive formation of a tetrahydrofuran ring from pentaallyl nitrone or nitrile oxide demonstrated the preferred formation of a five-membered ring to that of six or seven-membered rings. The nitrile oxide generated from a 3,4,5,6,7-pentaallyloxy-1-nitroheptane derivative obtained from pentaallylglucose underwent diastereoselective cycloaddition to give an isoxazoline fused to a pyran ring. Enantiopure isoxazoles containing tetrahydrofuran and oxepane rings were also prepared in good yields by the nitrile oxide cycloaddition of the 2-O- and 4-O-propargyl derivatives.

D-Galactofuranosylphosphonates. First Synthesis of UDP-C-D-galactofuranose

The chemical synthesis of two phosphono analogues of D-galactofuranosyl phosphate was performed. The natural phosphate seemed to be too labile to allow the chemical synthesis of UDP-Galf, these C-galactofuranosides are stable pharmacophores, and the α-phosphono analogue has been easily converted into UDP-C-Galf. UDP-C-Galf was tested as a competitive inhibitor of UDP-galactopyranose mutase and showed inhibition of Galf formation. Thus, it is of potential interest as an antimycobacterial agent; as an active molecule against Trypanosoma cruzi, the causative agent of South American trypanosomiasis (Chagas' disease), and as a stable analogue for use in UDP-galactopyranose mutase crystallization studies.

Structurally simplified zaragozic acid (squalestatin): Stereoselective preparation of a 3,4-unsubstituted derivative

Stereoselective preparation of a structurally simplified 3,4-unsubstituted zaragozic acid derivative was achieved starting from D-glucose. The present approach involved the stereoselective addition of a vinyl Grignard reagent, selective cleavage of 1,2-diol, and regioselective acylation of the hydroxyl group at C-6.