28512-68-7

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 
• 127066-70-0 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate 
• 439-03-2 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 145259-93-4 Phenyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-thio-β-D-glucopyranoside 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 14365-16-3 bis-(phenylthio)-dibutylstannane 
• 604-68-2 α-D-glucopyranose peracetylate 
• 930-69-8 sodium thiophenolate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 604-70-6 tetra-O-acetyl-1-O-methyl-β-D-glucopyranose 
• 74808-17-6 methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 107961-09-1 α-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,4,6-tetra-O-acetyl-D-glucopyranose 
• 100432-86-8 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 65615-62-5 Bromo-acetic acid (5R,6R)-5-acetoxy-6-acetoxymethyl-4-oxo-2-phenylsulfanyl-5,6-dihydro-4H-pyran-3-yl ester 
• 65615-61-4 D-Erythro-Hex-1-enopyranosid-3-ulose 
• 53438-23-6 phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranoside 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 211423-01-7 p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 124595-24-0 phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

TEMPO-Mediated Regiospecific Oxidation of Glucosides to Glucuronides

A TEMPO/hypochlorite/bromide oxidant has been used for the conversion of aryl and steroidal glucosides to the corresponding glucuronide conjugates in good (48-74%) yield. An isoflavone glucoside failed to undergo this transformation.

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

Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions

A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.

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.

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.

Total Synthesis of a Partial Structure from Arabinogalactan and Its Application for Allergy Prevention

Arabinogalactan, a microheterogeneous polysaccharide occurring in plants, is known for its allergy-protective activity, which could potentially be used for preventive allergy treatment. New treatment options are highly desirable, especially in a preventive manner, due to the constant rise of atopic diseases worldwide. The structural origin of the allergy-protective activity of arabinogalactan is, however, still unclear and isolation of the polysaccharide is not feasible for pharmaceutical applications due to a variation of the activity of the natural product and contaminations with endotoxins. Therefore, a pentasaccharide partial structure was selected for total synthesis and subsequently coupled to a carrier protein to form a neoglycoconjugate. The allergy-protective activity of arabinogalactan could be reproduced with the partial structure in subsequent in vivo experiments. This is the first example of a successful simplification of arabinogalactan with a single partial structure while retaining its allergy-preventive potential.

Rhamnogalacturonan II: Chemical Synthesis of a Substructure Including α-2,3-Linked Kdo**

The synthesis of a fully deprotected Kdo-containing rhamnogalacturonan II pentasaccharide is described. The strategy relies on the preparation of a suitably protected homogalacturonan tetrasaccharide backbone, through a post-glycosylation oxidation approach, and its stereoselective glycosylation with a Kdo fluoride donor.