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

• 74264-88-3 6-O-tert-butyldimethylsilanyl-1-O-methyl-β-D-glucopyranoside 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-tertbutyldimethylsilyl-β-D-glucopyranoside 
• 155049-46-0 methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 58479-67-7 methyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 
• 620-05-3 iodomethylbenzene 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 253596-67-7 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-[7-deoxy-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranos-7(E)-ylidene]-α-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 1220688-58-3 C₄₉H₅₁NO₆ 

Downstream Products

• 88677-01-4 methyl (methyl 2,3,4-tri-O-benzyl-α-D-mannopyranosid)uronate 
• 114933-63-0 C₃₅H₃₉O₈P 
• 160193-75-9 Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-5-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester 
• 81644-96-4 2,3,4-tri-O-benzyl-6-O-(3,4-di-O-benzyl-2-O-methylsulfonyl-α-L-rhamnopyranosyl)-α-D-mannopyranoside 
• 81644-95-3 2,3,4-tri-O-benzyl-6-O-(3,4-di-O-benzyl-2-O-methylsulfonyl-β-L-rhamnopyranosyl)-α-D-mannopyranoside 
• 76251-57-5 2,3,4-tri-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 113421-14-0 methyl (E)-2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-manno-oct-6-enodialdo-1,5-pyranoside 
• 115520-88-2 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-oct-6(E)-eno-α-D-manno-1,5-pyranoside 
• 186540-08-9 Acetic acid (2R,4aR,6S,7S,8S,8aR)-8-methoxy-2-phenyl-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 1053696-63-1 (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-[((2R,3S,4R,5R)-4-benzyloxy-2,5-bis-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-furan-3-yloxy)-(4-methoxy-phenyl)-methoxymethyl]-6-methoxy-tetrahydro-pyran 
• 203056-89-7 methyl 2,3,4-tri-O-benzyl-6-O-(4-methoxybenzyl)-α-D-mannopyranoside 
• 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 
• 208765-55-3 methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-benzyl-α-D-mannopyranoside 
• 111462-66-9 β-D-GlcpNAc-(1->6)-α-D-Manp-OMe 

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

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.

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.

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 of human syndecan-4 glycopeptide bearing O-, N-sulfation and multiple aspartic acids for probing impacts of the glycan chain and the core peptide on biological functions

Proteoglycans are a family of complex glycoproteins with glycosaminoglycan chains such as heparan sulfate (HS) attached to the core protein backbone. Due to the high structural heterogeneity of HS in nature, it is challenging to decipher the respective roles of the HS chain and the core protein on proteoglycan functions. While the sulfation patterns of HS dictate many activities, the core protein can potentially impact HS functions. In order to decipher this, homogeneous proteoglycan glycopeptides are needed. Herein, we report the first successful synthesis of proteoglycan glycopeptides bearing multiple aspartic acids in the core peptide and O- and N-sulfations in the glycan chain, as exemplified by the syndecan-4 glycopeptides. To overcome the high acid sensitivities of sulfates and base sensitivities of the glycopeptide during synthesis, a new synthetic approach has been developed to produce a sulfated glycan chain on a peptide sequence prone to the formation of aspartimide side products. The availability of the structurally well-defined synthetic glycopeptide enabled the investigation of their biological functions including cytokine, growth factor binding and heparanase inhibition. Interestingly, the glycopeptide exhibited context dependent enhancement or decrease of biological activities compared to the peptide or the glycan alone. The results presented herein suggest that besides varying the sulfation patterns of HS, linking the HS chain to core proteins as in proteoglycans may be an additional approach to modulate biological functions of HS in nature.

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-

Addressing the biochemical foundations of a glucose-based "trojan horse"-strategy to boron neutron capture therapy: From chemical synthesis to in vitro assessment

Boron neutron capture therapy (BNCT) for cancer is on the rise worldwide due to recent developments of in-hospital neutron accelerators which are expected to revolutionize patient treatments. There is an urgent need for improved boron delivery agents, and herein we have focused on studying the biochemical foundations upon which a successful GLUT1-targeting strategy to BNCT could be based. By combining synthesis and molecular modeling with affinity and cytotoxicity studies, we unravel the mechanisms behind the considerable potential of appropriately designed glucoconjugates as boron delivery agents for BNCT. In addition to addressing the biochemical premises of the approach in detail, we report on a hit glucoconjugate which displays good cytocompatibility, aqueous solubility, high transporter affinity, and, crucially, an exceptional boron delivery capacity in the in vitro assessment thereby pointing toward the significant potential embedded in this approach.