18685-19-3

Usage

Uses

Used in Organic Chemistry:
Methyl-6-O-trityl-2,3,4-tri-O-benzyl-α-D-glucopyranoside is used as a building block for the synthesis of more complex compounds and natural products. Its highly substituted and protected structure allows for selective modification and protection of specific hydroxyl groups, making it a valuable intermediate in the creation of various carbohydrate-based molecules.
Used in Pharmaceutical Industry:
Methyl-6-O-trityl-2,3,4-tri-O-benzyl-α-D-glucopyranoside is used as a key intermediate in the synthesis of pharmaceutical compounds, particularly those involving carbohydrate-based molecules. Its selective protection and modification capabilities enable the development of novel drug candidates with improved properties and therapeutic potential.
Used in Material Science:
Methyl-6-O-trityl-2,3,4-tri-O-benzyl-α-D-glucopyranoside is used in the development of advanced materials, such as glycopolymers and biomaterials, that have potential applications in various fields, including drug delivery, tissue engineering, and nanotechnology. Its unique structure and functional groups contribute to the design and synthesis of innovative materials with tailored properties and functions.

Upstream product

• 100-39-0 benzyl bromide 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 76-83-5 trityl chloride 
• 18311-26-7 methyl 6-O-triphenylmethyl-α-D-galactopyranoside 
• 20231-36-1 methyl 6-O-trityl-α-D-mannopyranoside 
• 100-44-7 benzyl chloride 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 3396-99-4 methyl α-D-galactopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 492-62-6 alpha-D-glucopyranose 
• 530-26-7 D-Mannose 

Downstream Products

• 55094-26-3 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 250127-77-6 methyl 2,3,4-tri-O-benzyl-6-O-(prop-2-ynyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of mannoheptose derivatives and their evaluation as inhibitors of the lectin LecB from the opportunistic pathogen Pseudomonas aeruginosa

Abstract Biofilm formation and chronic infections with Pseudomonas aeruginosa depend on lectins produced by the bacterium. The bacterial C-type lectin LecB binds to the two monosaccharides l-fucose and d-mannose and conjugates thereof. Previously, d-manno

Major increases of the reactivity and selectivity in aminoglycoside O-alkylation due to the presence of fluoride ions

Major increases of the selectivity and/or reactivity in aminosugar and sugar O-alkylation were observed in the presence of tetrabutylammonium fluoride (TBAF) in comparison to TBAI under phase-transfer conditions or in solution. The presence of TBAF allowe

USE OF MANNOSE 6 PHOSPHATE AND MODIFICATIONS THEREOF FOR MEMORY ENHANCEMENT AND REDUCING MEMORY IMPAIRMENT

Provided are compositions and methods for memory enhancement, including recovery of memory impairment. The compositions and methods relate to mannose-6-phosphate and derivatives of mannose-6-phosphate. The methods relate to administration of M6P or derivatives thereof to individuals in whom memory enhancement is desired.

Chemical synthesis and preliminary biological evaluation of C-6-O-methyl-1-deoxynojirimycin as a potent α-glucosidase inhibitor

A facile and efficient synthesis of 6-O-methyl-1-deoxynojirimycin 4 from commercially available methyl α-D-glucopyranoside in 10 steps and 25% overall yield was reported. The synthetic strategy was based on the regioselective protection/deprotection at 6-

USE OF IGF-2 RECEPTOR AGONIST LIGANDS FOR TREATMENT OF ANGELMAN SYNDROME AND AUTISM

Provided are methods for treatment of neurodevelopmental disorders, such as Angelman Syndrome and autism comprising administering to an individual a composition comprising an agonist ligand of IGF -2 receptor. The agonist ligand of IGF-2 receptor may be IGF -2, or mannose-6-phosphate or a derivative thereof. Compositions comprising mannose-6-phosphate derivatives are also disclosed.

Peptide-Coated Platinum Nanoparticles with Selective Toxicity against Liver Cancer Cells

Peptide-stabilized platinum nanoparticles (PtNPs) were developed that have significantly greater toxicity against hepatic cancer cells (HepG2) than against other cancer cells and non-cancerous liver cells. The peptide H-Lys-Pro-Gly-dLys-NH2 was identified by a combinatorial screening and further optimized to enable the formation of water-soluble, monodisperse PtNPs with average diameters of 2.5 nm that are stable for years. In comparison to cisplatin, the peptide-coated PtNPs are not only more toxic against hepatic cancer cells but have a significantly higher tumor cell selectivity. Cell viability and uptake studies revealed that high cellular uptake and an oxidative environment are key for the selective cytotoxicity of the peptide-coated PtNPs.

From d-to l-Monosaccharide Derivatives via Photodecarboxylation-Alkylation

Photodecarboxylation-alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in 21% yield over six steps.

Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation

A new organocatalytic glycosylation method exploiting the lactol functionality has been disclosed. The catalytic generation of glycosyl oxacarbenium ions from lactols under forcible conditions via weakly Br?nsted-acidic, readily available secondary amine salts affects the diastereoselective glycosylation of 2-deoxypyranoses and furanoses. This operationally simple iminium catalyzed activation of 2-deoxy hemi-acetals is a potential alternative to the existing cumbersome methods that need specialized handling. The mechanisms for this unique transformation and kinetic/thermodynamic effects have been discussed based on both experimental evidence and theoretical studies.

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside

We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.

Study of Uridine 5′-Diphosphate (UDP)-Galactopyranose Mutase Using UDP-5-Fluorogalactopyranose as a Probe: Incubation Results and Mechanistic Implications

Uridine 5′-diphosphate-5-fluorogalactopyranose (UDP-5F-Galp, 7) was synthesized, and its effect on UDP-Galp mutase (UGM) was investigated. UGM facilitated the hydrolysis of 7 to yield UDP and 5-oxogalactose (24), but no 11 was detected. 19F NMR and trapping experiments demonstrated that the reaction involves the initial formation of a substrate-cofactor adduct followed by decomposition of the resulting C5 gem-fluorohydrin to generate a 5-oxo intermediate (10). The results support the current mechanistic proposal for UGM and suggest new directions for designing mechanism-based inhibitors.