211678-08-9

Upstream product

• 211801-73-9 C₇₇H₉₀O₅SSi₄ 
• 100-39-0 benzyl bromide 
• 28244-94-2 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 1152-39-2 p-methylphenyl-1-thio-β-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 106-45-6 para-thiocresol 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 381715-17-9 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol 
• 220645-07-8 p-methylphenyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 
• 873298-76-1 p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 
• 918161-01-0 p-methylphenyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 
• 1206803-27-1 p-methylphenyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-1-thio-β-D-galactopyranoside 
• 1339956-62-5 p-methylphenyl 2,3,4-tri-O-benzyl-6-O-dimethylphenylsilyl-1-thio-β-D-galactopyranoside 
• 55094-26-3 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Mapping mechanisms in glycosylation reactions with donor reactivity: Avoiding generation of side products

The glycosylation reaction, which is key for the studies on glycoscience, is challenging due to its complexity and intrinsic side reactions. Thioglycoside is one of the most widely used glycosyl donors in the synthesis of complex oligosaccharides. However, one of the challenges is its side reactions, which lower its yield and limits its efficiency, thereby requiring considerable effort in the optimization process. Herein, we reported a multifaceted experimental approach that reveals the behaviors of side reactions, such as the intermolecular thioaglycon transformation and N-glycosyl succinimides, via the glycosyl intermediate. Our mechanistic proposal was supported by low temperature NMR studies that can further be mapped by utilizing relative reactivity values. Accordingly, we also presented our findings to suppress the generation of side products in solving this particular problem for achieving high-yield glycosylation reactions.

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Solid-phase synthesis is a practical approach for simplifying the time-consuming and routine purification steps in the preparation of numerous naturally occurring molecules; however, studying such reactions is difficult due to the lack of a convenient monitoring method. By using thin-layer chromatography in conjunction with a photolabile linker on a resin, we developed a convenient and simple method for monitoring solid-phase reactions in real time by thin-layer chromatography. This method provides a user-friendly protocol for examining reaction conditions for solid-state syntheses.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS

Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery

Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(IV) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(IV) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 μM) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.

Anthrax capsule surface carbohydrate antigen-based novel trisaccharide 4-methoxyphenoside compound and preparation method thereof

The invention relates to an anthrax capsule surface carbohydrate antigen-based novel trisaccharide 4-methoxyphenoside compound and a preparation method thereof. The structural formula of the trisaccharide 4-methoxyphenoside compound is shown in the description; and in the formula, R1 is an acetyl group, R2 is a benzyl group, R3 is an acetamido group, and the end position is a p-methylphenoxyl group. The compound can be used for preparing oligosaccharide-like conjugates, can be used for synthesis reaches of anthrax carbohydrate vaccines, has the advantages of concise synthesis route, simplicity in operation, low raw material cost, strong versatility, and good glycosylation reaction stereoselectivity, and is suitable for synthesizing various oligosaccharide compounds.

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.

A Kinsenoside and GoodyerosideA analogs of the preparation and use thereof

The invention discloses a preparation method and application of compounds as shown in formula I and II, and in particular relates to preparation of Kinsenoside or GoodyerosideA analogue and medical application of the Kinsenoside or GoodyerosideA analogue

CARBOHYDRATE-MODIFIED GLYCOPROTEINS AND USES THEREOF

The present invention provides immunogenic compounds which stimulate immune responses in a subject. The present invention provides compositions comprising an isolated glycoprotein antigen covalently bound at pre-existing carbohydrate residues present on the glycoprotein to a carbohydrate epitope. The present invention also provides a method to induce an immune response in a subject comprising administering the compounds of the invention. The present invention further provides methods of making the compounds of the invention and methods of using the compounds of the invention to stimulate immune responses to infectious disease agents and tumors.