183901-63-5

Usage

Uses

Used in Pharmaceutical Industry:
.alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate) is used as a key intermediate in the synthesis of mannosyl-based dendrimers. These dendrimers are multi-branched, nano-scale polymers that can be employed as drug delivery systems, enhancing the solubility, stability, and bioavailability of various therapeutic agents. The unique structure of these dendrimers allows for the precise control of their size, shape, and surface properties, making them versatile platforms for drug development.
Used in Antimicrobial Applications:
.alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate) is also used as an inhibitor for treating microbial infections. .alpha.-D-Mannopyranose, 2,3,4,6-tetrabenzoate 1-(2,2,2-trichloroethanimidate) can interfere with the biosynthesis of bacterial cell walls, specifically targeting the enzymes involved in the synthesis of peptidoglycan, a major component of the cell wall. By inhibiting this process, the compound can effectively disrupt the structural integrity of bacterial cells, leading to their death and preventing the spread of infections.

Upstream product

• 545-06-2 trichloroacetonitrile 
• 627466-98-2 2,3,4,6-tetra-O-benzoyl-α,β-D-mannospyranose 
• 41308-76-3 allyl α-D-mannopyranoside 
• 7296-15-3 alpha-D-mannopyranoside 
• 98-88-4 benzoyl chloride 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside 
• 96996-90-6 1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside 
• 64768-20-3 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 

Downstream Products

• 198276-43-6 C₅₅H₆₀O₁₂ 
• 444709-80-2 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose 
• 495390-51-7 2-[2-(2-chloroethoxy)ethoxy]ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 495390-31-3 3-(methoxycarbonyl)propyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 612057-01-9 allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 612060-33-0 3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2-O-isopropylidene-α-D-glucofuranose 
• 914803-30-8 (2S,3R,4E)-2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyl-(1'->1)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol 
• 869747-72-8 C₆₆H₇₈O₁₂ 
• 942270-75-9 3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)oxymethyluridine 
• 1001403-85-5 methyl 2,4-di-O-benzoyl-3,6-di-O-(6-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy]-4-thiahexyl)-α-D-mannopyranoside 
• 1001403-71-9 methyl 2,4-di-O-benzoyl-3,6-di-O-(3-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy]-propyl)-α-D-mannopyranoside 
• 692739-18-7 2-bromoethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 1355331-86-0 5-(N-benzyloxycarbonyl)aminopentyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Oligomannoside mimetics by glycosylation of 'octopus glycosides' and their investigation as inhibitors of type 1 fimbriae-mediated adhesion of Escherichia coli

The glycocalyx of eukaryotic cells is composed of glycoconjugates, which carry highly complex oligosaccharide portions. To elucidate the biological role and function of the glycocalyx in cell-cell communication and cellular adhesion processes, glycomimeti

New lipophilic glycomimetic DC-SIGN ligands: Stereoselective synthesis and SPR-based binding inhibition assays

The design and synthesis of efficient ligands for DC-SIGN is a topic of high interest, because this C-type lectin has been implicated in the early stages of many infection processes. DC-SIGN membrane-protein presents four carbohydrate-binding domains (CRD) that specifically recognize mannose and fucose. Therefore, antagonists of minimal disaccharide epitope Manα(1,2)Man, represent potentially interesting antibacterial and antiviral agents. In the recent past, we were able to develop efficient antagonists, mimics of the natural moiety, characterized by the presence of a real D-carbamannose unit which confers greater stability to enzymatic breakdown than the corresponding natural disaccharide ligand. Herein, we present the challenging stereoselective synthesis of four new amino or azide glycomimetic DC-SIGN antagonists with attractive orthogonal lipophilic substituents in C(3), C(4) or C(6) positions of the real carba unit, which were expected to establish crucial interactions with lipophilic areas of DC-SIGN CRD. The activity of the new ligands was evaluated by SPR binding inhibition assays. The interesting results obtained, allow to acquire important information about the influence of the lipophilic substituents present in specific positions of the carba scaffold. Furthermore, C(6) benzyl C(4) tosylamide pseudodisaccharide displayed a good affinity for DC-SIGN with a more favorable IC50 value than those of the previously described real carba-analogues. This study provides valuable knowledge for the implementation of further structural modifications towards improved inhibitors.

Synthesis of Carbohydrate-Centered Oligosaccharide Mimetics Equipped with a Functionalized Tether

Synthetic glycoclusters have gained substantial attention as mimetics of multivalent glycoconjugates. For their proposed glycobiological applications, it is advantageous to incorporate a functionalized tether into the clusters, which allows coupling to so

Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides

The allylic bromination of allyl glycosides is conducted using NBS/AIBN reagents in (EtO)2CO and PhCF3 solutions, without using CCl4 as a solvent. The activated mixed halo-allyl glycosides led to glycosylations, mediated by a triflate, in a latent-active

Synthesis of a Glycosylphosphatidylinositol (GPI) Fragment as a Potential Substrate for Mannoprotein Transglycosidases

A glycophosphatidylinositol tetrasaccharide fragment was synthesized to mimic the core features of primary model, that of Saccharomyces cerevisiae. The salient feature of this approach is centered on the quick access to various α-1,2- and α-1,6-mannosyl a

GLUCOSE-RESPONSIVE INSULIN CONJUGATES

Glucose-responsive insulin conjugates that contain one or more trisaccharides are provided. Such insulin conjugates may display a pharmacokinetic (PK) and/or pharmacodynamic (PD) profile that is responsive to the systemic concentrations of a saccharide such as glucose or alpha-methylmannose, even when administered to a subject in need thereof in the absence of an exogenous multivalent saccharide-binding molecule.

The dehydroepiandrosterone and dehydroepiandrosterone alkone glycosylation derivative and its preparation method and application

The invention discloses epiandrosterone glycosylation derivatives and dehydrogenated epiandrosterone glycosylation derivatives, and a preparation method thereof. The preparation method comprises the following steps: respectively carrying out coupling reac

3 - monosaccharide acid oxygen glucoside oleanolic alkane type and wusu alkane triterpene saponin derivative and its preparation method and application

The invention discloses a 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative. The derivative has a structural formula as shown in the specification, wherein R4 is one of H atom, alkyl containing 1-10 carbons, alkyl

36 branchings honeydews five sugar six sugar-to methoxyphenyl glycoside and its preparation method and application

The invention provides a 3,6-branched mannopentaose and hexaose on methoxy phenyl glycoside and a preparation method and an application thereof. A structural formula is shown in a formula I or a formula II; a compound can be used for preparing anti-HIV me

Saccharide-modified nanodiamond conjugates for the efficient detection and removal of pathogenic bacteria

The detection and removal of bacteria, such as E. coli in aqueous environments by using safe and readily available means is of high importance. Here we report on the synthesis of nanodiamonds (ND) covalently modified with specific carbohydrates (glyco-ND) for the precipitation of type 1 fimbriated uropathogenic E. coli in solution by mechanically stable agglutination. The surface of the diamond nanoparticles was modified by using a Diels-Alder reaction followed by the covalent grafting of the respective glycosides. The resulting glyco-ND samples are fully dispersible in aqueous media and show a surface loading of typically 0.1 mmol g-1. To probe the adhesive properties of various ND samples we have developed a new sandwich assay employing layers of two bacterial strains in an array format. Agglutination experiments in solution were used to distinguish unspecific interactions of glyco-ND with bacteria from specific ones. Two types of precipitates in solution were observed and characterized in detail by light and electron microscopy. Only by specific interactions mechanically stable agglutinates were formed. Bacteria could be removed from water by filtration of these stable agglutinates through 10 μm pore-size filters and the ND conjugate could eventually be recovered by addition of the appropriate carbohydrate. The application of glycosylated ND allows versatile and facile detection of bacteria and their efficient removal by using an environmentally and biomedically benign material. Copyright