53008-65-4

Usage

Uses

Used in Organic Synthesis:
Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside is used as a key intermediate in the synthesis of various complex organic molecules, particularly in the field of carbohydrate chemistry. Its benzyl-protected structure allows for selective functionalization and manipulation of the molecule, facilitating the construction of more intricate carbohydrate structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside is utilized as a building block for the development of novel drug candidates. Its unique structure and reactivity enable the creation of new molecules with potential therapeutic applications, such as antibiotics, antivirals, and anticancer agents.
Used in Material Science:
Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside also finds applications in material science, where it can be used to develop new polymers and materials with specific properties. Its ability to form complex structures and interact with other molecules makes it a promising candidate for the development of advanced materials with applications in various industries, such as electronics, automotive, and aerospace.
Used in Research and Development:
In academic and industrial research settings, Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside serves as an important compound for studying the fundamental aspects of carbohydrate chemistry and its role in biological systems. It is also used as a reference material for the development and optimization of new synthetic methods and techniques in organic chemistry.

InChI:InChI=1/C28H32O6/c1-30-28-27(33-20-23-15-9-4-10-16-23)26(32-19-22-13-7-3-8-14-22)25(24(17-29)34-28)31-18-21-11-5-2-6-12-21/h2-16,24-29H,17-20H2,1H3/t24-,25-,26+,27-,28+/m1/s1

Upstream product

• 67583-56-6 Methyl 2,3,4-O-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 13035-24-0 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 67412-01-5 Methyl 6-O-triphenylmethyl-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 620-05-3 iodomethylbenzene 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-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 
• 492-62-6 alpha-D-glucopyranose 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 

Downstream Products

• 85011-35-4 1-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranose 
• 82231-39-8 methyl 2,3,4-tri-O-benzyl-6-O-methyl-β-D-glucopyranoside 
• 170639-48-2 (1R,2S,3S,4R,5S)-2,3,4-Tris-benzyloxy-5-hydroxymethyl-cyclopentanol 
• 230620-32-3 (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite 
• 244286-92-8 methyl 2,3,4-tri-O-benzyl-6-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 354797-81-2 methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 164026-05-5 methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-β-D-glucopyranoside 
• 1057491-43-6 C₆₉H₇₅NO₂₇ 
• 90124-29-1 methyl [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranosyl)onate]-(2→6)-2,3,4-tri-O-benzyl-β-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.

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.

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

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.

KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot

A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is

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.

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.

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

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.