68779-52-2

Usage

Uses

1. Used in Organic Synthesis:
2,3,5-Tri-O-benzyl-1-O-(4-nitrobenzoyl)-D-arabinofuranose is used as an intermediate in the synthesis of various complex organic molecules. Its unique structure allows for selective functionalization and modification, making it a valuable building block in the development of new compounds with potential applications in various industries.
2. Used in Pharmaceutical Research:
In the pharmaceutical industry, 2,3,5-Tri-O-benzyl-1-O-(4-nitrobenzoyl)-D-arabinofuranose is used as a key component in the development of novel drug candidates. Its unique chemical properties enable the design of new molecules with potential therapeutic applications, such as antibiotics, antivirals, and anticancer agents.
3. Used in Material Science:
2,3,5-TRI-O-BENZYL-1-O-(4-NITROBENZOYL)-D-ARABINOFURANOSE's unique structure and properties also make it a candidate for use in the development of new materials with specific properties. For example, it could be used in the synthesis of new polymers or as a component in the development of advanced materials with applications in electronics, energy storage, or other high-tech industries.
4. Used in Chemical Research:
2,3,5-Tri-O-benzyl-1-O-(4-nitrobenzoyl)-D-arabinofuranose is also used as a research tool in the study of various chemical reactions and processes. Its unique structure allows chemists to investigate the mechanisms of various reactions, leading to a better understanding of organic chemistry and the development of new synthetic methods.

InChI:InChI=1/C30H34O7/c1-30(31-2)36-28-27(34-20-24-16-10-5-11-17-24)26(33-19-23-14-8-4-9-15-23)25(35-29(28)37-30)21-32-18-22-12-6-3-7-13-22/h3-17,25-29H,18-21H2,1-2H3

Upstream product

• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 29073-91-4 (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 
• 83-87-4 D-Mannose pentaacetate 
• 67-56-1 methanol 
• 13242-53-0 acetobromomannose 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 50801-29-1 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-α-D-galactopyranose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 

Downstream Products

• 69435-20-7 C₅₀H₆₂O₉ 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 138925-14-1 phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 152871-96-0 phenyl 1-deoxy-2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 213028-88-7 1-O-acetyl-3,4,6-tri-O-benzyl-α,β-D-glucopyranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 384819-72-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 858108-96-0 N-(benzyloxycarbonyl)aminopropyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 858109-02-1 N-(benzyloxycarbonyl)aminopropyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranoside 
• 858108-98-2 N-(benzyloxycarbonyl)aminopropyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-mannopyranoside 
• 858109-00-9 N-(benzyloxycarbonyl)aminopropyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-mannopyranoside 
• 858109-06-5 [N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate 
• 952139-86-5 [N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate 

Relevant academic research and scientific papers

Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates

Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har

ANTIBODY CONJUGATES AND METHODS OF MAKING THE ANTIBODY CONJUGATES

Described herein are antibody conjugates and methods of making antibody conjugates.

Exploring glycosylation reactions under continuous-flow conditions

The industrial development of carbohydrate-based drugs is greatly thwarted by the typical challenges inherent in oligosaccharide synthesis. The practical advantages of continuous-flow synthesis in microreactors (high reproducibility, easy scalability, and fast reaction optimization) may offer an effective support to make carbohydrates more attractive targets for drug-discovery processes. Here we report a systematic exploration of the glycosylation reaction carried out under microfluidic conditions. Trichloroacetimidates and thioglycosides have been investigated as glycosyl donors, using both primary and secondary acceptors. Each microfluidic glycosylation has been compared with the corresponding batch reaction, in order to highlight advantages and drawbacks of microreactors technology. As a significant example of multistep continuous-flow synthesis, we also describe the preparation of a trisaccharide by means of two consecutive glycosylations performed in interconnected microreactors.

Synthetic oligosaccharides as tools to demonstrate cross-reactivity between polysaccharide antigens

Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colitis, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide

Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation

In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra

Neighboring-group participation by C-2 ether functions in glycosylations directed by nitrile solvents

Ether-protecting functions at C-2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C-2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2-cis glycosyl oxazolinium intermediate is formed. This participation, in conjunction with the anomeric effect of the glycosyl donor, confers high 1,2-trans selectivities on glycosylations. Further application of this concept has led to efficient preparations of α-(1→5)-arabinan oligomers.

1,2-Anhydrosaccharides and 1,2-cyclic sulfites as saccharide donors in convergent synthesis of glucopyranosyl-, mannopyranosyl- and ribofuranosylbenzocamalexin

A convergent synthesis of 1-(β-o-glucopyranosyl)-, 1-(α-D-mannopyranosyl)- and 1-(β-D-ribofuranosyl) benzocamalexin was elaborated as an alternative route to the linear approach based on the indoline-indole method. 1,2-Anhydrosaccharides and 1,2-cyclic sulfites as saccharide donors were used in the key glycosylation step. Coupling with benzocamalexin resulted in moderate to excellent yields of nucleoside analogs, depending on the saccharide donor, catalyst and solvent used.

Sex pheromones of the hair crab Erimacrus isenbeckii. II. Synthesis of ceramides

To confirm their structures and to assess the pheromonal activity, novel ceramides, possible sex pheromones of the hair crab Erimacrus isenbeckii, were synthesized from D-galactose. The synthetic ceramides were identical with the natural ceramides.

A convenient multigram preparation of functionalized 2-azido-2-deoxy-D-mannose as a useful orthogonally protected building block for oligosaccharide synthesis

Multigram preparation of strategically protected 2-azido-2-deoxy mannose 5 from pentaacetyl glucose 1 is described. This manno-derivative was obtained in a straightforward manner and in high overall yield and represents a flexible building-block for complex oligosaccharide synthesis.

Synthesis and enzymatic evaluation of modified acceptors of recombinant blood group A and B glycosyltransferases

The disaccharide α-L-Fucp-(1→2)-β-D-Galp-(1→O)-Octyl (1) is an acceptor for the human blood group A and B glycosyltransferases. Seven analogues of 1, containing deoxy, methoxy and arabino modifications of the Fuc residue, were chemically synthesized and kinetically evaluated in radioactive enzymatic assays. Both the enzymes tolerate modification of the 3'-OH on the fucose residue. The 2'-OH was found to be key to the recognition of the acceptors by these enzymes. The arabino derivative was recognized as an acceptor by the A transferase (K(m) of 200 μM), but not the B transferase and is the first synthetic acceptor capable of distinguishing between the two enzyme activities. (C) 2000 Elsevier Science Ltd.