99409-34-4

Usage

Uses

Used in Organic Synthesis:
ETHYL 2,3,4-TRI-O-BENZYL-1-THIO-BETA-L-FUCOPYRANOSIDE is used as a fucosyl donor in glycosylation reactions for the synthesis of complex oligosaccharides and other carbohydrate-based structures. Its benzyl-protected thiol functionality provides stability and reactivity, making it a valuable reagent in organic synthesis.
Used in Carbohydrate Chemistry:
In the field of carbohydrate chemistry, ETHYL 2,3,4-TRI-O-BENZYL-1-THIO-BETA-L-FUCOPYRANOSIDE is used as a key building block for the construction of various carbohydrate structures. Its unique properties allow for the formation of glycosidic bonds, which are essential for the synthesis of biologically active carbohydrates and their derivatives.
Used in Pharmaceutical Research:
ETHYL 2,3,4-TRI-O-BENZYL-1-THIO-BETA-L-FUCOPYRANOSIDE is used as a starting material in the development of new pharmaceutical compounds, particularly those targeting carbohydrate-based drug discovery. Its ability to form complex oligosaccharides makes it a promising candidate for the synthesis of novel therapeutic agents.
Used in Biochemical Research:
In biochemical research, ETHYL 2,3,4-TRI-O-BENZYL-1-THIO-BETA-L-FUCOPYRANOSIDE is used as a tool to study the role of carbohydrates in biological processes. Its ability to modify carbohydrates and create complex structures allows researchers to investigate the interactions between carbohydrates and other biomolecules, such as proteins and lipids.
Used in Material Science:
ETHYL 2,3,4-TRI-O-BENZYL-1-THIO-BETA-L-FUCOPYRANOSIDE is used in the development of carbohydrate-based materials, such as hydrogels and polymers, for various applications in material science. Its unique properties enable the creation of materials with specific properties, such as biocompatibility, biodegradability, and stimuli-responsiveness.
Used in Analytical Chemistry:
In analytical chemistry, ETHYL 2,3,4-TRI-O-BENZYL-1-THIO-BETA-L-FUCOPYRANOSIDE is used as a reference compound for the development and validation of analytical methods for the detection and quantification of carbohydrates and their derivatives. Its well-defined structure and properties make it an ideal standard for calibration and quality control purposes.

InChI:InChI=1/C29H34O4S/c1-3-34-29-28(32-21-25-17-11-6-12-18-25)27(31-20-24-15-9-5-10-16-24)26(22(2)33-29)30-19-23-13-7-4-8-14-23/h4-18,22,26-29H,3,19-21H2,1-2H3/t22-,26+,27+,28-,29+/m0/s1

Upstream product

• 6696-41-9 alpha-L-fucose 
• 100-39-0 benzyl bromide 
• 75-08-1 ethanethiol 
• 69558-02-7 Ethyl 2,3,4-tri-O-acetyl-1-thio-α/β-L-fucopyranoside 
• 100-44-7 benzyl chloride 
• 132799-10-1 ethyl 1-thio-α-L-fucopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 

Downstream Products

• 116415-24-8 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-glucopyranoside 
• 116391-15-2 methyl 2,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-galactopyranoside 
• 126330-72-1 (3aR,4R,6S,7S,7aR)-4-Methoxy-2,2,6-trimethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 126330-72-1 (3aR,4R,6S,7S,7aR)-4-Methoxy-2,2,6-trimethyl-7-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 131337-93-4 (3aR,4S,6R,7S,7aR)-6-Methoxy-2,2,4-trimethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 162222-93-7 (1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol 
• 189323-03-3 Piperidine-1,4-dicarboxylic acid 4-ethyl ester 1-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyl] ester 
• 184829-86-5 C₇₈H₇₇NO₁₉ 
• 221005-08-9 methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside 
• 227749-88-4 phenyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 257286-47-8 methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside 
• 157488-87-4 thexyldimethylsilyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 286420-46-0 N-[(2R,4aR,6R,7R,8R,8aS)-6-Octyloxy-2-phenyl-8-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 353233-31-5 C₇₂H₇₆O₁₆ 

Relevant academic research and scientific papers

Pillar[5]arene-Based Polycationic Glyco[2]rotaxanes Designed as Pseudomonas aeruginosa Antibiofilm Agents

Pseudomonas aeruginosa (P.A.) is a human pathogen belonging to the top priorities for the discovery of new therapeutic solutions. Its propensity to generate biofilms strongly complicates the treatments required to cure P.A. infections. Herein, we describe the synthesis of a series of novel rotaxanes composed of a central galactosylated pillar[5]arene, a tetrafucosylated dendron, and a tetraguanidinium subunit. Besides the high affinity of the final glycorotaxanes for the two P.A. lectins LecA and LecB, potent inhibition levels of biofilm growth were evidenced, showing that their three subunits work synergistically. An antibiofilm assay using a double δlecAδlecB mutant compared to the wild type demonstrated that the antibiofilm activity of the best glycorotaxane is lectin-mediated. Such antibiofilm potency had rarely been reached in the literature. Importantly, none of the final rotaxanes was bactericidal, showing that their antibiofilm activity does not depend on bacteria killing, which is a rare feature for antibiofilm agents.

A preparation 1-S -2, 3, 4-tri-O-benzyl-l-sulfur generation of pyrane Gorgy xylosides method

The invention provides a method for preparing 1-S-2,3,4-tri-o-benzyl-1-sulfo-pyran fucus glycoside. The method comprises the following steps of: adding DMF (Dimethyl Formamide), sodium borohydride, zinc chloride and blue copperas into a reaction container; dripping benzyl chloride in a stirring manner; dripping 1-S-ethyl-1-sulfo-pyran fucus glycoside after the dripping of the benzyl chloride; and after the material adding, reacting at a room temperature and performing aftertreatment, thereby obtaining the 1-S-2,3,4-tri-o-benzyl-1-sulfo-pyran fucus glycoside. Thus, the method which does not require NaH (Sodium Hydride) participated in the reaction and is moderate in reaction, high in safe coefficient and high in yield is provided.

Total synthesis of LewisX using a late-stage crystalline intermediate

Abstract Herein, we report on a highly efficient synthesis of a crystalline protected LewisX trisaccharide that was converted to LewisX following global deprotection. The trisaccharide was prepared in a highly convergent synthesis (seven steps, longest linear sequence) and in a 38% overall yield using a strategy that involved the regioselective glycosylation of a GlcNAc acceptor with a galactose thioglycoside donor, followed by fucosylation of the remaining free GlcNAc hydroxyl as key steps. The core trisaccharide also has the potential to be converted to other members of the Type-2 Lewis family of antigens due to the orthogonal nature of the protecting groups employed.

Synthesis and biological evaluation of a library of glycoporphyrin compounds

A library of glycosylated porphyrins (glycoporphyrins) was prepared and the compounds were evaluated for their photodynamic therapy (PDT) activity against the oesophageal squamous-cell carcinoma cell line OE21 in vitro. A synthetic methodology was develop

A new approach to explore the binding space of polysaccharide-based ligands: Selectin antagonists

The discovery of molecules that interfere with the binding of a ligand to a receptor remains a topic of great interest in medicinal chemistry. Herein, we report that a monosaccharide unit of a polysaccharide ligand can be replaced advantageously by a conformationally locked acyclic molecular entity. A cyclic component of the selectin ligand Sialyl Lewisx, GlcNAc, is replaced by an acyclic tether, tartaric esters, which link two saccharide units. The conformational bias of this acyclic tether originates from the minimization of intramolecular dipole-dipole interaction and the gauche effect. The evaluation of the binding of these derivatives to P-selectin was measured by surface plasmon resonance spectroscopy. The results obtained in our pilot study suggest that the discovery of tunable tethers could facilitate the exploration of the carbohydrate recognition domain of various receptors.

The design, synthesis, and evaluation of novel conformationally rigid analogues of sialyl Lewis(x)

The design and synthesis of a series of analogues of sialyl Lewis(x) (1) which incorporate conformationally rigid tetralin and naphthalene ring systems (2-4) has led to novel compounds which have similar potency to 1 as inhibitors of cell adhesion. Copyright (C) 1998 Elsevier Science Ltd.

Synthesis of a tri- and a hepta-saccharide which contain alpha-L-fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins.

Reaction of a thioglycoside with methyl trifluoromethanesulfonate (methyl triflate) in the presence of a hydroxyl compound is an efficient glycosylation method. Thus, methyl triflate-promoted condensation of ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1