51103-66-3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 66224-56-4 methyl 6-azido-6-deoxy-α-D-mannopyranoside 
• 108825-73-6 C₂₁H₂₆O₁₀S₂ 
• 18439-60-6 methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 121424-20-2 1,2,3,4-tetra-O-acetyl-6-(4-methylbenzenesulfonate)-α-D-mannopyranose 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-D-rhamnopyranoside 
• 872352-30-2 methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-lyxohexopyran-4-uloside 
• 172688-40-3 (5R,6S,7R)-5,6,7-trihydro-5-(1R-1-hydroxyethyl)-6,7-O-isopropylidenepyrrolo<1,2-d>tetrazole-6,7-diol 
• 68396-86-1 methyl 6-deoxy-6-tert-butoxycarbonylamino-β-D-glucopyranoside 
• 138332-00-0 6-azido-6-deoxy-D-mannopyranose 
• 7512-03-0 methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-D-mannopyranoside 
• 108825-78-1 methyl 2,3-di-O-benzoyl-4,6-di-O-p-tolylsulfonyl-α-D-mannopyranoside 
• 79695-15-1 methyl 6-amino-6-deoxy-α-D-mannopyrannoside 
• 112612-45-0 methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 92528-09-1 methyl 6-azido-6-deoxy-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

TBAF Effects 3,6-Anhydro Formation from 6-O-Tosyl Pyranosides

3,6-Anhydro sugars are common structures in algal polysaccharides and occur in the furanodictine and sauropunol natural products. We have found that treatment of 6-O-tosylpyranosides with tetrabutylammonium fluoride provides a mild, high-yielding synthesis of 3,6-anhydro sugars. Using O-glycoside substrates, 3,6-anhydropyranosides are isolated and the use of N,O-dimethyl hydroxylamine glycosides yields 3,6-anhydrofuranosides. Applying this approach, concise synthetic routes to several 3,6-anhydro sugar natural products are reported, including furanodictine A and sauropunols A-D.

Sweet Drugs for Bad Bugs: A Glycomimetic Strategy against the DC-SIGN-Mediated Dissemination of SARS-CoV-2

The C-type lectin receptor DC-SIGN is a pattern recognition receptor expressed on macrophages and dendritic cells. It has been identified as a promiscuous entry receptor for many pathogens, including epidemic and pandemic viruses such as SARS-CoV-2, Ebola virus, and HIV-1. In the context of the recent SARS-CoV-2 pandemic, DC-SIGN-mediated virus dissemination and stimulation of innate immune responses has been implicated as a potential factor in the development of severe COVID-19. Inhibition of virus binding to DC-SIGN, thus, represents an attractive host-directed strategy to attenuate overshooting innate immune responses and prevent the progression of the disease. In this study, we report on the discovery of a new class of potent glycomimetic DC-SIGN antagonists from a focused library of triazole-based mannose analogues. Structure-based optimization of an initial screening hit yielded a glycomimetic ligand with a more than 100-fold improved binding affinity compared to methyl α-d-mannopyranoside. Analysis of binding thermodynamics revealed an enthalpy-driven improvement of binding affinity that was enabled by hydrophobic interactions with a loop region adjacent to the binding site and displacement of a conserved water molecule. The identified ligand was employed for the synthesis of multivalent glycopolymers that were able to inhibit SARS-CoV-2 spike glycoprotein binding to DC-SIGN-expressing cells, as well as DC-SIGN-mediated trans-infection of ACE2+ cells by SARS-CoV-2 spike protein-expressing viruses, in nanomolar concentrations. The identified glycomimetic ligands reported here open promising perspectives for the development of highly potent and fully selective DC-SIGN-targeted therapeutics for a broad spectrum of viral infections.

Synthesis and in vitro investigation of potential antiproliferative monosaccharide–D-secoestrone bioconjugates

The syntheses of monosaccharide–D-secoestrone conjugates are reported. They were prepared from 3-(prop-2-inyloxy)-D-secoestrone alcohol or oxime and monosaccharide azides via Cu(I)-catalyzed azide–alkyne cycloaddition reactions (CuAAC). The antiproliferat

Synthesis of modified D-mannose core derivatives and their impact on GH38 α-mannosidases

Nine new compounds having five- and modified six-member carbohydrate core derived from D-lyxose or D-mannose, and non-hydrolysable aglycones (benzylsulfonyl or aryl(alkyl)triazolyl) were synthesised to investigate their ability to inhibit the recombinant

New [(η5-C5H5)Ru(N-N)(PPh3)][PF6] compounds: Colon anticancer activity and GLUT-mediated cellular uptake of carbohydrate-appended complexes

Eight ruthenium(ii) compounds of the general formula [(η5-C5H5)Ru(N-N)(PPh3)][PF6] were rationally designed, exhibiting high cytotoxicity against HCT116 human colon cancer cells, with IC50

Synthesis and binding affinity analysis of positional thiol analogs of mannopyranose for the elucidation of sulfur in different position

Synthetic routes towards thio-α/β-d-mannose derivatives are presented. Double parallel or double serial inversion was successfully applied in the efficient synthesis of 2-thio- or 2,4-di-thio-mannoside derivatives. The protein recognition properties of th

Importance of topology for glycocluster binding to Pseudomonas aeruginosa and Burkholderia ambifaria bacterial lectins

Pseudomonas aeruginosa (PA) and Burkholderia ambifaria (BA) are two opportunistic Gram negative bacteria and major infectious agents involved in lung infection of cystic fibrosis patients. Both bacteria can develop resistance to conventional antibiotherap

GLYCOMIMETICS AS PSEUDOMONAS AERUGINOSA LECTIN INHIBITORS

The present invention relates to fucose- and mannose-derived glycomimetics and their general use in prophylaxis or treatment of Pseudomonas aeruginosa infections including respiratory tract infections, urinary tract infections, nosocomial infections and chronic wound infections in a patient encompassing a patient suffering already from cystic fibrosis. Said glycomimetics are inhibitors of Pseudomonas aeruginosa lectin LecB.

Glycomimetics as pseudomonas Aeruginosa lectin inhibitors

The present invention relates to fucose- and mannose-derived glycomimetics and their general use in prophylaxis or treatment of Pseudomonas aeruginosa infections including respiratory tract infections, urinary tract infections, nosocomial infections and chronic wound infections in a patient encompassing a patient suffering already from cystic fibrosis. Said glycomimetics are inhibitors of Pseudomonas aeruginosa lectin LecB.

Towards a stable noeuromycin analog with a d-manno configuration: Synthesis and glycosidase inhibition of d-manno-like tri- and tetrahydroxylated azepanes

Noeuromycin is a highly potent albeit unstable glycosidase inhibitor due to its hemiaminal function. While stable d-gluco-like analogs have been reported, no data are available for d-manno-like structures. A series of tri- and tetrahydroxylated seven-memb