66224-56-4

Usage

Uses

Used in Organic Synthesis:
(3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL serves as a valuable intermediate in organic synthesis, particularly for the development of complex organic molecules and pharmaceutical agents. Its azide and methoxy functionalities can be strategically utilized in various synthetic transformations, making it a versatile building block for creating novel compounds with diverse applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL is employed as a key component in the design and synthesis of potential drug candidates. Its unique stereochemistry and functional groups can be exploited to create molecules with specific biological activities, targeting various therapeutic areas such as oncology, infectious diseases, and neurological disorders.
Used in Chemical Biology:
(3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL also finds application in chemical biology, where it can be used to probe and manipulate biological systems. Its azide group, in particular, can be employed in click chemistry approaches to label biomolecules or construct bioconjugates, enabling the study of biological processes and the development of new diagnostic and therapeutic tools.

Upstream product

• 51103-66-3 methyl 6-O-(p-tolylsulfonyl)-α-D-mannopyranoside 
• 20744-42-7 methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxy-α-D-mannopyranoside 
• 87586-20-7 2,4,6-Trimethyl-benzenesulfonic acid (2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 92528-09-1 methyl 6-azido-6-deoxy-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 18439-60-6 methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 18439-61-7 methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-mannopyranoside 
• 139978-81-7 methyl 2,3-O-isopropylidene-α-D-mannopyranoside 4,6-sulfite 
• 139978-82-8 methyl-2,3-O-isopropylidene-4,6-cyclic sulfate-α-D-mannopyranoside 
• 63167-69-1 methyl 2,3-O-isopropylidene-α-D-mannopyranoside 
• 4990-80-1 Methyl-6-chlor-6-deoxy-α-D-mannopyranosid 

Downstream Products

• 79695-15-1 methyl 6-amino-6-deoxy-α-D-mannopyrannoside 
• 138332-00-0 6-azido-6-deoxy-D-talose 
• 66224-57-5 methyl 6-azido-6-deoxy-2,3-di-O-benzylidene-α-D-mannopyranoside 
• 68396-86-1 methyl 6-deoxy-6-tert-butoxycarbonylamino-β-D-glucopyranoside 
• 1354049-02-7 (3aS,4S,5aR,11aR,11bS)-8-(4-chlorophenyl)-4-methoxy-2,2-dimethyl-10-phenyl-3a,4,5a,6,11a,11b-hexahydro[1,3]dioxolo[4,5]pyrano[3,2-b][1,5]oxazocine 
• 1354049-03-8 (3aS,4S,5aR,11aR,11bS)-4-methoxy-2,2-dimethyl-10-phenyl-8-(2-thienyl)-3a,4,5a,6,11a,11b-hexahydro[1,3]dioxolo[4,5]pyrano[3,2-b][1,5]oxazocine 
• 1354049-05-0 (3aS,4S,5aR,11aR,11bS)-4-methoxy-2,2-dimethyl-8,10-diphenyl-3a,4,5a,6,11a,11b-hexahydro[1,3]dioxolo[4,5]pyrano[3,2-b][1,5]oxazocine 
• 1354049-06-1 (3aS,4S,5aR,11aR,11bS)-8-(3-flurophenyl)-4-methoxy-2,2-dimethyl-10-phenyl-3a,4,5a,6,11a,11b-hexahydro[1,3]dioxolo[4,5]pyrano[3,2-b][1,5]oxazocine 
• 1446093-34-0 C₁₉H₂₇N₃O₅ 
• 1446093-35-1 C₁₅H₁₈FN₃O₅ 
• 1446093-46-4 methyl 6-(phenylsulfonylamido)-6-deoxy-α-D-mannopyranoside 
• 1446093-36-2 C₁₄H₂₁NO₅ 
• 1446093-37-3 C₁₄H₂₀N₂O₇ 
• 1446093-38-4 C₁₅H₂₀N₂O₅ 

Relevant academic research and scientific papers

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.

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

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

Gold nanoparticles decorated with mannose-6-phosphate analogues

Herein, the preparation of neoglycoconjugates bearing mannose-6-phosphate analogues is described by: (a) synthesis of a cyclic sulfate precursor to access the carbohydrate head-group by nucleophilic displacement with an appropriate nucleophile; (b) introduction of spacers on the mannose-6-phosphate analogues via Huisgen's cycloaddition, the Julia reaction, or the thiol-ene reaction under ultrasound activation. With the resulting compounds in hand, gold nanoparticles could be functionalized with various carbohydrate derivatives (glycoconjugates) and then tested for angiogenic activity. It was observed that the length and flexibility of the spacer separating the sugar analogue from the nanoparticle have little influence on the biological response. One particular nanoparticle system substantially inhibits blood vessel growth in contrast to activation by the corresponding monomeric glycoconjugate, thereby demonstrating the importance of multivalency in angiogenic activity.

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.

Discovery of two classes of potent glycomimetic inhibitors of pseudomonas aeruginosa LecB with distinct binding modes

The treatment of infections due to the opportunistic pathogen Pseudomonas aeruginosa is often difficult, as a consequence of bacterial biofilm formation. Such a protective environment shields the bacterium from host defense and antibiotic treatment and secures its survival. One crucial factor for maintenance of the biofilm architecture is the carbohydrate-binding lectin LecB. Here, we report the identification of potent mannose-based LecB inhibitors from a screening of four series of mannosides in a novel competitive binding assay for LecB. Cinnamide and sulfonamide derivatives are inhibitors of bacterial adhesion with up to a 20-fold increase in affinity to LecB compared to the natural ligand methyl mannoside. Because many lectins of the host require terminal saccharides (e.g., fucosides), such capped structures as reported here may offer a beneficial selectivity profile for the pathogenic lectin. Both classes of compounds show distinct binding modes at the protein, offering the advantage of a simultaneous development of two new lead structures as anti-pseudomonadal drugs with an anti-virulence mode of action.

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

Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models

Methyl amino-deoxy-glycosides with α- and β-gluco, α-galacto, or α-manno stereochemistry with the amino functionality in each of the four possible non-anomeric positions have been synthesized and their pKa values determined by titration. These