7464-38-2

Upstream product

• 91-60-1 2-Naphthalenethiol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 5586-15-2 bis(2-naphthyl)disulfide 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 

Downstream Products

• 1469428-05-4 2-naphthyl 3-(3-phenyl-1-hydroxy)-1-thio-β-D-galactopyranoside 
• 1469428-06-5 2-naphthyl 3-(3-(aniline)-2-propyn-1-hydroxyl)-1-thio-β-D-galactopyranoside 
• 3971-48-0 1,5-anhydro-D-galactitol 

Relevant academic research and scientific papers

Aromatic thioglycoside inhibitors against the virulence factor LecA from Pseudomonas aeruginosa

Three small families of hydrolytically stable thioaryl glycosides were prepared as inhibitors of the LecA (PA-IL) virulence factor corresponding to the carbohydrate binding lectin from the bacterial pathogen Pseudomonas aeruginosa. The monosaccharidic arylthio β-d-galactopyranosides served as a common template for the major series that was also substituted at the O-3 position. Arylthio disaccharides from lactose and from melibiose constituted the other two series members. In spite of the fact that the natural ligand for LecA is a glycolipid of the globotriaosylceramide having an α-d-galactopyranoside epitope, this study illustrated that the β-d-galactopyranoside configuration having a hydrophobic aglycon could override the requirement toward the anomeric configuration of the natural sugar. The enzyme linked lectin assay together with isothermal titration microcalorimetry established that naphthyl 1-thio-β-d-galactopyranoside (11) gave the best inhibition with an IC 50 twenty-three times better than that of the reference methyl α-d-galactopyranoside. In addition it showed a KD of 6.3 μM which was ten times better than that of the reference compound. The X-ray crystal structure of LecA with 11 was also obtained.

Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate. The reaction conditions are reasonably simple and yields were very good.

Synthesis of thioglycosides in room temperature ionic liquid

An eco-friendly reaction for the preparation of thioglycosides has been developed using an ionic liquid as the solvent. Thioglycosides were obtained in excellent yields on treatment of per-O-acetylated sugar derivatives with thiols in the presence of boro

Odorless preparation of thioglycosides and Thio-Michael adducts of carbohydrate derivatives

A general, odorless, one-pot methodology has been developed for the preparation of 1,2-trans-thioglycosides and thio-Michael addition products of carbohydrate derivatives through triphenyl phosphine-mediated cleavage of disulfides and reaction of the thio

Mechanistic studies and methods to prevent aglycon transfer of thioglycosides

Thioglycosides have been employed extensively for the synthesis of complex oligosaccharides, carbohydrate libraries, and mimetics of O-glycosides. While very useful, aglycon transfer is a problematic side reaction with thioglycosides. In this paper, a series of mechanistic studies are described. The aglycon transfer process is shown to affect both armed and disarmed thioglycosides, cause anomerization of the carbon-sulfur bond of a thioglycoside, and destroy the product of a glycosylation reaction. The results indicate that the aglycon transfer process can be a major problem for a wide range of thioglycosides. This side reaction is especially important to consider when carrying out complex reactions such as solid-phase glycosylations, one-pot or orthogonal multicomponent glycosylations, and construction of carbohydrate libraries. To prevent transfer, a number of modified aglycons were examined. The 2,6-dimethylphenyl (DMP) aglycon was found to effectively block transfer in a variety of model studies and glycosylation reactions. The DMP group can be installed in one step from a commercially available thiol (2,6- dimethylthiophenol) and is useable as a glycosyl donor. On the basis of these features, the DMP group is proposed as a convenient and improved aglycon for thioglycosides.

Aryl O- and S-galactosides and lactosides as specific inhibitors of human galectins-1 and -3: Role of electrostatic potential at O-3

Phase transfer catalyzed reaction was used for the high yielding synthesis of aryl 1-thio-β-d-galacto- and lacto-pyranosides carrying a panel of substituents on the phenyl groups. Best galectin-1 inhibitors were simple p-nitrophenyl thiogalactoside 5a for

Ready access to sialylated oligosaccharide donors

(figure presented) Numerous glycoconjugates contain the disaccharide Neu5Acα(2→S)DGalp. An efficient way to incorporate this disaccharide into synthetic glycoconjugates is to develop a disaccharide building block. This communication reports a chemoenzymatic route to such a building block which requires as few as four steps. Some examples using more chemical steps are also presented, which increase the flexibility. These disaccharide donors were used to prepare synthetic trisaccharides.