116514-50-2

Upstream product

• 6696-41-9 alpha-L-fucose 
• 100-39-0 benzyl bromide 
• 75-08-1 ethanethiol 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 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 
• 179601-56-0 (3R,4S,5R,6R)-2-Ethylsulfanyl-6-methyl-tetrahydro-pyran-3,4,5-triol 
• 156769-28-7 methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranoside 
• 50711-27-8 methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside 
• 13231-27-1 Methyl-2,3-di-O-benzyl-6-desoxy-α-D-galactopyranosid 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 868381-78-6 (2S,3R,4S,5R,6R)-2-Ethylsulfanyl-6-methyl-tetrahydro-pyran-3,4,5-triol 
• 179601-55-9 ethyl 2,3,4-tri-O-acetyl-1-thio-D-fucopyranoside 

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 
• 137063-49-1 C₅₅H₆₀O₁₀ 
• 116391-17-4 methyl 4,6-di-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-D-mannopyranoside 
• 137063-46-8 C₆₁H₆₄O₁₀ 
• 137063-45-7 C₆₁H₆₄O₁₀ 
• 33639-77-9 perbenzyl fucosyl bromide 
• 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 
• 162118-38-9 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 
• 162222-93-7 (1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol 
• 172147-74-9 Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl ester 
• 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 

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.

A divergent approach to the synthesis of iGb3 sugar and lipid analogues via a lactosyl 2-azido-sphingosine intermediate

Isoglobotrihexosylceramide (iGb3, 1) is an immunomodulatory glycolipid that binds to CD1d and is presented to the T-cell receptor (TCR) of invariant natural killer T (iNKT) cells. To investigate how modifications to the lipid tail or terminal sugar residu

Synthesis of L-altrose and some derivatives

A convenient approach to the chemical synthesis of L-altrose (1) and its 6-deoxy derivative 2 has been developed by starting from D-galactose (9) and D-fucose (10), respectively. The 5-epimerization by a Mitsunobu inversion of the open-chain D-hexoses was the key step for these routes. Furthermore, the conversion of 2 into peracetylated TDP-6-deoxy-α-L-altrose (3a) was achieved by the cycloSal approach. However, the final deacetylation led to an unexpected side-reaction resulting in the previously unknown 6-deoxy-α-L-altropyranose 1,3-cyclophosphate (4).

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.

Mirror-Image Carbohydrates: Synthesis of the Unnatural Enantiomer of a Blood Group Trisaccharide

Methyl D-glucoside and D-glucose pentaacetate are transformed, respectively, into methyl α-O-glucuronide 3 and hydroxymethyl β-C-glucuronide 9, which undergo decarboxylative elimination efficiently to produce 4-deoxypentenoside 4 and L-glucal 10. These unsaturated pyranosides provide an expeditious entry into mirror-image oligosaccharides, as demonstrated in the synthesis of the unnatural enantiomer of the H-type II blood group determinant trisaccharide (D-Fuc-(α1-2)-L-Gal-(β 1-4)-L-GlcNAc-β-OMe). This work illustrates that D-glucose, a common starting material in the synthesis of naturally occurring carbohydrates, can also be used to prepare their mirror-image analogues.

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 double-chain bis-sulfone neoglycolipids of the 2''-, 3''-, 4''-, and 6''-deoxyglobotrioses

2-(Trimethylsilyl)ethyl (Me3SiCH2CH2) 2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-benzoyl-6-O-p-methoxybenzyl-β-D-galactopyranosyl-β-D-glucopyranoside was glycosylated with different 2-, 3-, 4-, or 6-"deoxy-D-galactose" derivatives to give the corresponding deoxytr