86782-39-0

Upstream product

• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 108-24-7 acetic anhydride 
• 108-98-5 thiophenol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 14365-16-3 bis-(phenylthio)-dibutylstannane 
• 604-68-2 α-D-glucopyranose peracetylate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 882-33-7 diphenyldisulfane 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 19879-84-6 tetraacetyl thioglucose 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 17314-33-9 tributyltin phenyl sulfide 

Downstream Products

• 87470-73-3 phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 120403-27-2 phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 861927-81-3 phenyl 2,3,4-tri-O-benzyl-1-thio-6-O-trityl-β-D-glucopyranoside 
• 158411-89-3 [(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-yl]-methanol 
• 158411-90-6 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid 
• 158411-91-7 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 173655-37-3 Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 134296-61-0 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 1293912-47-6 C₂₇H₂₃NO₇S 
• 1293912-52-3 C₆₁H₄₉NO₁₆S 
• 1293912-54-5 phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→3)-1-thio-β-D-glucopyranoside 
• 1293912-53-4 C₃₃H₃₃NO₁₂S 
• 1293912-48-7 2-[4-(7,8-dihydroxy-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-2-yl)-phenyl]-benzo[f]isoindole-1,3-dione 
• 1293912-49-8 C₃₁H₂₅NO₇S 

Relevant academic research and scientific papers

HClO4-SiO2 catalyzed per-O-acetylation of carbohydrates

An efficient per-O-acetylation of carbohydrates catalyzed by HClO 4-SiO2 is reported using a stoichiometric quantity of acetic anhydride avoiding the use of pyridine and excess acetic anhydride under solvent-free conditions.

Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**

Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

Fighting Shigella by Blocking Its Disease-Causing Toxin

Shiga toxin is an AB5 toxin produced by Shigella species, while related toxins are produced by Shiga toxin-producing Escherichia coli (STEC). Infection by Shigella can lead to bloody diarrhea followed by the often fatal hemolytic uremic syndrome (HUS). In the present paper, we aimed for a simple and effective toxin inhibitor by comparing three classes of carbohydrate-based inhibitors: glycodendrimers, glycopolymers, and oligosaccharides. We observed a clear enhancement in potency for multivalent inhibitors, with the divalent and tetravalent compounds inhibiting in the millimolar and micromolar range, respectively. However, the polymeric inhibitor based on galabiose was the most potent in the series exhibiting nanomolar inhibition. Alginate and chitosan oligosaccharides also inhibit Shiga toxin and may be used as a prophylactic drug during shigella outbreaks.

Carbohydrate-Based NK1R Antagonists with Broad-Spectrum Anticancer Activity

NK1R antagonists, investigated for the treatment of several pathologies, have shown encouraging results in the treatment of several cancers. In the present study, we report on the synthesis of carbohydrate-based NK1R antagonists and their evaluation as anticancer agents against a wide range of cancer cells. All of the prepared compounds, derived from either-arabinose, have shown high affinity and NK1R antagonistic activity with a broad-spectrum anticancer activity and an important selectivity, comparable to Cisplatin. This strategy has allowed us to identify the galactosyl derivative 14α , as an interesting hit exhibiting significant NK1R antagonist effect (kinact0.209 ± 0.103 μM) and high binding affinity for NK1R (IC50= 50.4 nM,Ki= 22.4 nM by measuring the displacement of [125I] SP from NK1R). Interestingly, this galactosyl derivative has shown marked selective cytotoxic activity against 12 different types of cancer cell lines.

NEW IMMUNOSTIMULATORS AND USE THEREOF IN IMMUNOTHERAPY

The present invention relates to a new family of iNKT stimulators, referred to as 6"-O-PEGm-NHR-GalCer, which are potent analogues of KRN7000. These iNKT stimulators can advantageously be used in therapy, in particular for the prevention and/or treatment of many diseases requiring a stimulation of an immune response, such as cancer, viral, bacterial or parasitic diseases, autoimmune diseases or inflammatory diseases. The iNKT cell stimulator of the invention may be coupled to a biological carrier, such as a therapeutic and/or targeting agent, or be vectorized, for example in nanoparticles, to be specifically delivered to target cells.

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

The assembly of complex bacterial glycans presenting rare structural motifs and cis-glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions i

How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?

The reaction of glycosyl donor phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with NIS/TfOH(cat.) was systematically studied under various reaction conditions. Neither the molecular sieve pore size nor amount of NIS activator was found to have a

Chemical Synthesis and Biological Evaluations of Adiponectin Collagenous Domain Glycoforms

The homogeneously glycosylated 76-amino acid adiponectin collagenous domains (ACDs) with all of the possible 15 glycoforms have been chemically and individually synthesized using stereoselective glycan synthesis and chemical peptide ligation. The following biological and pharmacological studies enabled correlating glycan pattern to function in the inhibition of cancer cell growth as well as the regulation of systemic energy metabolism. In particular, hAdn-WM6877 was tested in detail with different mouse models and it exhibited promising in vivo antitumor, insulin sensitizing, and hepatoprotective activities. Our studies demonstrated the possibility of using synthetic glycopeptides as the adiponectin downsized mimetic for the development of novel therapeutics to treat diseases associated with deficient adiponectin.

Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature

A mild, convenient and transition-metal-free protocol for the synthesis of aryl 1-thioglycosides is presentedviaarynes generatedin situcombined with glycosyl thiols in the presence of TBAF(tBuOH)4. The methodology provides a general and efficient way to prepare a series of functionalized thioglycosides in good to excellent yields with a perfect control of the anomeric configuration at room temperature. In addition, the reaction conditions tolerate a variety of the pentoses and hexoses, and the reaction also performs smoothly on protected monosaccharides and disaccharides.