641635-63-4

Usage

Uses

Used in Organic Synthesis:
Methyl 2,3,4-Tri-O-benzyl-D-galactopyranoside is used as a synthetic intermediate for the development of various complex organic compounds. Its application in organic synthesis is attributed to its unique structure, which allows for the creation of a wide range of derivatives with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3,4-Tri-O-benzyl-D-galactopyranoside is used as a key building block for the synthesis of glycoconjugates, which are essential in the development of drugs targeting various diseases. Its role in the synthesis of these complex molecules is crucial for enhancing their efficacy and selectivity.
Used in Chemical Research:
Methyl 2,3,4-Tri-O-benzyl-D-galactopyranoside is also employed in chemical research as a model compound for studying the reactivity and properties of similar sugar derivatives. This helps researchers gain a better understanding of the underlying chemical mechanisms and develop new strategies for the synthesis of novel compounds with potential applications in various fields.
Used in Material Science:
In the field of material science, Methyl 2,3,4-Tri-O-benzyl-D-galactopyranoside can be used as a component in the development of advanced materials with specific properties, such as improved biocompatibility or enhanced mechanical strength. Its unique chemical structure allows for the creation of new materials with tailored properties for various applications.

Upstream product

• 67583-56-6 Methyl 2,3,4-O-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside 
• 101312-02-1 methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 
• 2595-06-4 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran 
• 100-44-7 benzyl chloride 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 194149-26-3 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 83051-88-1 methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 114219-26-0 methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside 
• 82231-38-7 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 

Downstream Products

• 4356-79-0 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 147687-33-0 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 88677-01-4 methyl (methyl 2,3,4-tri-O-benzyl-α-D-mannopyranosid)uronate 
• 203056-89-7 methyl 2,3,4-tri-O-benzyl-6-O-(4-methoxybenzyl)-α-D-mannopyranoside 
• 111462-66-9 β-D-GlcpNAc-(1->6)-α-D-Manp-OMe 
• 1192366-21-4 C₄₈H₄₇Cl₄NO₁₅ 
• 1192366-15-6 C₆₂H₅₈O₁₅ 
• 208758-71-8 Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester 
• 75336-65-1 methyl 2,3,4-tri-O-benzyl-α-D-glucopyranuronate 
• 128503-39-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 129729-48-2 methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 129729-32-4 methyl 2,3,4-tri-O-benzyl-6-O-<3,4,6-tri-O-acetyl-2-(1-cyano-1-p-methoxyphenylmethylamino)-2-deoxy-α-D-glucopyranosyl>-α-D-glucopyranoside 
• 129729-50-6 methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 129729-49-3 methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-p-nitrobenzylideneamino-β-D-glucopyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Photolabile 2-(2-Nitrophenyl)-propyloxycarbonyl (NPPOC) for Stereoselective Glycosylation and Its Application in Consecutive Assembly of Oligosaccharides

A photolabile protecting group (PPG) 2-(2-nitrophenyl)-propyloxycarbonyl (NPPOC) was explored in glycosylation and applied in the consecutive synthesis of oligosaccharides. NPPOC displays a strong neighboring group participation (NGP) effect to facilitate the construction of 1,2-trans glycosides in excellent yield. Notably, NPPOC could be efficiently removed by photolysis, and the deprotection conditions are friendly to typical protecting groups. A branched and asymmetric oligomannose Man6 was rapidly prepared, and the consecutive assembly of oligosaccharides without intermediate purification was further investigated owing to the compatibility conditions between NPPPOC's photolysis and glycosylation.

Substrate Substitution in Kanosamine Biosynthesis Using Phosphonates and Phosphite Rescue

Kanosamine is an antibiotic and antifungal compound synthesized from glucose 6-phosphate (G6P) inBacillus subtilisby the action of three enzymes: NtdC, which catalyzes NAD-dependent oxidation of the C3-hydroxyl; NtdA, a PLP-dependent aminotransferase; and

Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides

A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is

Me3SI-promoted chemoselective deacetylation: a general and mild protocol

A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

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.

Mapping mechanisms in glycosylation reactions with donor reactivity: Avoiding generation of side products

The glycosylation reaction, which is key for the studies on glycoscience, is challenging due to its complexity and intrinsic side reactions. Thioglycoside is one of the most widely used glycosyl donors in the synthesis of complex oligosaccharides. However, one of the challenges is its side reactions, which lower its yield and limits its efficiency, thereby requiring considerable effort in the optimization process. Herein, we reported a multifaceted experimental approach that reveals the behaviors of side reactions, such as the intermolecular thioaglycon transformation and N-glycosyl succinimides, via the glycosyl intermediate. Our mechanistic proposal was supported by low temperature NMR studies that can further be mapped by utilizing relative reactivity values. Accordingly, we also presented our findings to suppress the generation of side products in solving this particular problem for achieving high-yield glycosylation reactions.

Carbocyclic Substrate Analogues Reveal Kanosamine Biosynthesis Begins with the α-Anomer of Glucose 6-Phosphate

NtdC is an NAD-dependent dehydrogenase that catalyzes the conversion of glucose 6-phosphate (G6P) to 3-oxo-glucose 6-phosphate (3oG6P), the first step in kanosamine biosynthesis in Bacillus subtilis and other closely-related bacteria. The NtdC-catalyzed r

A Potent Mimetic of the Siglec-8 Ligand 6’-Sulfo-Sialyl Lewisx

Siglecs are members of the immunoglobulin gene family containing sialic acid binding N-terminal domains. Among them, Siglec-8 is expressed on various cell types of the immune system such as eosinophils, mast cells and weakly on basophils. Cross-linking of Siglec-8 with monoclonal antibodies triggers apoptosis in eosinophils and inhibits degranulation of mast cells, making Siglec-8 a promising target for the treatment of eosinophil- and mast cell-associated diseases such as asthma. The tetrasaccharide 6’-sulfo-sialyl Lewisx has been identified as a specific Siglec-8 ligand in glycan array screening. Here, we describe an extended study enlightening the pharmacophores of 6’-sulfo-sialyl Lewisx and the successful development of a high-affinity mimetic. Retaining the neuraminic acid core, the introduction of a carbocyclic mimetic of the Gal moiety and a sulfonamide substituent in the 9-position gave a 20-fold improved binding affinity. Finally, the residence time, which usually is the Achilles tendon of carbohydrate/lectin interactions, could be improved.

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-