127501-41-1

Basic information

• Product Name: ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE
• Synonyms: ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE;Ethyl 2,3,4-tri-O-acetyl-b-L-thiofucopyranoside;ethyl-2,3,4-triacetyl--L-thifucopyranoside;Ethyl 6-deoxy-1-thio-beta-L-galactopyranoside 2,3,4-triacetate;Ethyl 6-deoxy-1-thio-beta-L-galactopyranoside triacetate
• CAS NO: 127501-41-1
• Molecular Formula: C₁₄H₂₂O₇S
• Molecular Weight: 334.38528
• Mol File: 127501-41-1.mol

Chemical Properties

• Melting Point: 78-79℃ (ethanol )
• Appearance: /
• CAS DataBase Reference: ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE(127501-41-1)
• EPA Substance Registry System: ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE(127501-41-1)

Safety Data

• Hazardous Substances Data: 127501-41-1(Hazardous Substances Data)

Upstream product

• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 75-08-1 ethanethiol 
• 108-24-7 acetic anhydride 
• 24332-96-5 2,3,4-Tri-O-acetyl-α-L-fucopyranosyl chloride 
• 811-51-8 sodium thioethylate 
• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 64913-16-2 L-fucose tetraacetate 
• 6696-41-9 alpha-L-fucose 
• 73-34-7 6-deoxy-L-galactose 
• 60-29-7 diethyl ether 
• 3615-37-0 D-Fucose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-β-L-fucopyranose 
• 13224-93-6 β-L-fucopyranose 
• 75247-29-9 (2R,3S,4R,5R,6S)-2-bromo-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate 

Downstream Products

• 129948-10-3 methyl 2-O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 116391-14-1 Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 25019-69-6 methyl 4-O-benzyl-α-L-rhamnopyranoside 
• 137438-95-0 Methyl 2-O-acetyl-4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside 
• 137439-12-4 C₆₀H₆₀O₂₂ 
• 135129-62-3 Methyl 3,4-di-O-benzoyl-2-O-(2,3,4-tri-O-benzoyl-α-L-fucopyranosyl)-α-L-rhamnopyranoside 
• 137171-20-1 Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 190248-99-8 ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside 
• 152015-42-4 S-ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside 
• 138343-56-3 ethyl 2-O-benzyl-1-thio-β-L-fucopyranoside 
• 190248-98-7 ethyl 2,4-di-O-benzyl-1-thio-β-L-fucopyranoside 
• 138343-55-2 ethyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 138343-58-5 ethyl 4-O-acetyl-2,3-di-O-benzyl-1-deoxy-1-thio-β-L-fucopyranoside 
• 283587-70-2 ethyl 2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside 

Relevant articles and documents

A facile synthesis of armed and disarmed colitose thioglycosides

Ethyl 2,4-di-O-acetyl-3,6-dideoxy-1-thio-β-L-xylohexopyranoside (10) and ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xyl0-hexopyranoside (12) were synthesized in 60% and 55% overall yield, respectively. Starting from α-L-fucose, sequential peracetylation

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.

Effect of Anomeric Configuration on Stereocontrolled α-Glycosylation of l -Fucose

In this letter, we report an approach to the stereoselective α-glycosylation of l -fucose that is exemplified by effect of anomeric configuration. The neighboring group participation is not compatible with α-glycosylation of l -fucose, therefore the remote participation by 4- O -Bz was employed to control the formation of 1,2- cis -glycosidic bond. Furthermore, we found the anomeric configuration of fucose donor is crucial to stereoselectivity of the glycosylated products. The α/β-mixed products were generated by using β-anomeric donor while the glycosyl donor in α configuration yielded products in high α-selectivity possibly due to the distinct pathway to forming the key intermediates. This phenomenon supplies the basis for the synthesis of complicated natural carbohydrates containing fucose α-glycoside, such as fucoidans, fucosylated N -glycans, and fucosylated chondroitin sulfates, etc.

METHOD FOR PREPARING 2'-O-FUCOSYLLACTOSE

The present invention relates to a method for preparing 2'-O-fucosyllactose and to the protected fucosyl donor of the formula (I) used in this method. The method comprises reacting the fucose derivative of the formula (I) below with the compound of the ge

Chemical Synthesis of a Glycopeptide Derived from Skp1 for Probing Protein Specific Glycosylation

Skp1 is a cytoplasmic and nuclear protein, best known as an adaptor of the SCF family of E3-ubiquitin ligases that label proteins for their degradation. Skp1 in Dictyostelium is posttranslationally modified on a specific hydroxyproline (Hyp) residue by a pentasaccharide, which consists of a Fucα1,2-Galβ-1,3-GlcNAcα core, decorated with two α-linked Gal residues. A glycopeptide derived form Skp1 was prepared to characterize the α-galactosyltransferase (AgtA) that mediates the addition of the α-Gal moieties, and to develop antibodies suitable for tracking the trisaccharide isoform of Skp1 in cells. A strategy was developed for the synthesis of the core trisaccharide-Hyp based on the use of 2-naphthylmethyl (Nap) ethers as permanent protecting groups to allow late stage installation of the Hyp moiety. Tuning of glycosyl donor and acceptor reactivities was critical for achieving high yields and anomeric selectivities of glycosylations. The trisaccharide-Hyp moiety was employed for the preparation of the glycopeptide using microwave-assisted solid phase peptide synthesis. Enzyme kinetic studies revealed that trisaccharide-Hyp and trisaccharide-peptide are poorly recognized by AgtA, indicating the importance of context provided by the native Skp1 protein for engagement with the active site. The trisaccharide-peptide was a potent immunogen capable of generating a rabbit antiserum that was highly selective toward the trisaccharide isoform of full-length Skp1. Antibody tracking: A glycopeptide containing a trisaccharide-hydroxyproline moiety was synthesized to characterize the substrate requirements of α-galactosyltransferase (AgtA) that mediates the addition of the α-Gal residues to the glycan of the glycoprotein Skp1 and to develop antibodies suitable for tracking the trisaccharide isoform of Skp1 in cells.

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.

INFLAMMATION IMAGING AND THERAPY

An imaging agent comprising a conjugate of an oligosaccharide moiety with an imaging moiety. The oligosaccharide is Lewis A or Lewis B or a mimetic thereof, or a pharmaceutically acceptable salt or PEGylated form of Lewis A or Lewis B or its mimetics. Lewis A and Lewis B and its mimetics are also provided for use in the therapeutic treatment of inflammatory diseases, autoimmune diseases and cancer.

Synthesis of benzaldehyde-functionalized LewisX trisaccharide analogs for glyco-SAM formation

LewisX (Lex) antigen based carbohydrate-carbohydrate interactions are mediated by complexation of metal ions. Although theoretical studies about the influence of participating hydroxyl groups in the Le x trisaccharide head group (Gal

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.