71676-30-7

Upstream product

• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 152983-23-8 phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 108-98-5 thiophenol 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 13992-16-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 124477-08-3 phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 87470-72-2 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 175977-99-8 phenyl 6-O-benzyl-1-thio-β-D-galactopyranoside 
• 208644-75-1 phenyl 2,3-di-O-benzoyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 179072-68-5 phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides

This article describes studies on the regioselective acetal protection of monosaccharide-based diols using chiral phosphoric acids (CPAs) and their immobilized polymeric variants, (R)-Ad-TRIP-PS and (S)-SPINOL-PS, as the catalysts. These catalyst-controll

N -Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides

The synthesis of glycopyranosyl nucleosides modified in the sugar moiety has been less frequently explored, notably because of the lack of a reliable method to glycosylate pyrimidine bases. Herein we report a solution in the context of the synthesis of peptidonucleosides. They were obtained after glycosylation of different pyrimidine nucleobases with glucopyranosyl donors carrying an azide group at the C4 position. A methodological study involving different anomeric leaving groups (acetate, phenylsulfoxide and ortho-hexynylbenzoate) showed that a sulfoxide donor in combination with trimethylsilyl triflate as the promoter led to the best yields.

Total Synthesis of the Echinodermatous Ganglioside LLG-3 Possessing the Biological Function of Promoting the Neurite Outgrowth

A total synthesis of echinodermatous ganglioside LLG-3 with neuritogenic activity was accomplished by a convergent strategy. The synthesis of 2-hydroxyethyl 8-O-Me-α-sialoside 2 was started from the phenyl 7,8-di-O-Pico-thiosialoside 5, which can be chemoselectively removed the picoloyl group, and then the methyl group in 8-O-MeNeu5Ac moiety was chemoselectively prepared using TMSCHN2/FeCl3. For preparation of the terminal disialic unit, oxidative amidation was initially utilized by our group to efficiently construct the α(2,11) linkage of 8-O-Me-Neu5Acα(2,11)Neu5Gc. Herein, we also demonstrate that the synthesized ganglioside LLG-3 exhibited the neuritogenic activity toward the primary cortical neurons and that biological activity is superior to that of ganglioside DSG-A.

Studies towards the total synthesis of repeating unit of O-sulfated polysaccharide from marine bacterium Cobetia pacifica KMM 3878

Herein we report assembly of the appropriately protected trisaccharide repeating unit of Cobetia pacifica KMM 3878 O-sulfated polysaccharide. Our synthesis involves 3,4-O-pyruvilated galactose as the key building block which acts as a donor as well as acceptor in the construction of trisaccharide. We obtained the R isomer as a major stereoisomer in the pyruvilation reaction. The glycosylations proceeded with high stereo and regioselectivity.

Synthesis of Glycosylated 1-Deoxynojirimycins Starting from Natural and Synthetic Disaccharides

Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bioorganic chemistry and medicinal chemistry, yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1-deoxynojirimycin derivatives based on the oxidation–reductive amination protocol that in the past has also been shown to be a versatile route towards 1-deoxynojirimycin. The strategy can be applied on commercial disaccharides, as shown in four examples, as well as on disaccharides that are not commercially available and are synthesized for this purpose, as shown by a fifth example.

Conformationally Switchable Glycosyl Donors

Glycosyl donors functionalized with 2,2′-bipyridine moieties on the 3-OH and 6-OH or the 2-OH and 4-OH undergo a conformational change when forming 1:1 complexes with Zn2+ ions. The pyranoside ring of the zinc complexes adopted axial-rich skew boat conformations. The reactivities of the two glycosyl donors were investigated by performing a series of glycosylations in the presence or absence of Zn2+ ions. These glycosylations suggested a decrease in reactivity when binding Zn2+. The conformational effect of binding Zn2+ was therefore studied using a third glycosyl donor, unable to undergo conformational changes when binding Zn2+. From competition experiments, it was observed that the binding-induced conformational change increased the reactivity slightly compared to the glycosyl donor unable to undergo a conformational change.

Molecular-Level Understanding of the Major Fragmentation Mechanisms of Cellulose Fast Pyrolysis: An Experimental Approach Based on Isotopically Labeled Model Compounds

Evaluation of the feasibility of various mechanisms possibly involved in cellulose fast pyrolysis is challenging. Therefore, selectively 13C-labeled cellotriose, 18O-labeled cellobiose, and 13C- and 18O-doubly-labeled cellobiose were synthesized and subjected to fast pyrolysis in an atmospheric pressure chemical ionization source of a linear quadrupole ion trap/orbitrap mass spectrometer. The initial products were immediately quenched, ionized using ammonium cations, and subsequently analyzed using the mass spectrometer. The loss or retention of isotope labels upon pyrolysis unambiguously revealed three major competing mechanisms - sequential losses of glycolaldehyde/ethenediol molecules from the reducing end (the reducing-end unraveling mechanism), hydroxymethylene-assisted glycosidic bond cleavage (HAGBC mechanism), and Maccoll elimination. Important discoveries include the following: (1) Reducing-end unraveling is the predominant mechanism occurring at the reducing end; (2) Maccoll elimination facilitates the cleaving of aglyconic bonds, and it is the mechanism leading to formation of reducing carbohydrates; 3) HAGBC occurs for glycosides but not at the reducing end of cellodextrins; 4) HAGBC and water loss are the predominant reactions for fast pyrolysis of 1,6-anhydrocellodextrins; and 5) HAGBC can proceed after reducing-end unraveling but unraveling does not occur once the HAGBC reaction pathway is initiated. Moreover, hydrolysis was conclusively ruled out for fast pyrolysis of cellobiose, cellotriose, and 1,6-anhydrocellodextrins up to cellotetraosan. No radical reactions were observed.

Synthesis, biological evaluation and structure-activity relationship studies of hederacolchiside E and its derivatives as potential anti-Alzheimer agents

Inspired by the previously reported neuroprotective activity of hederacolchiside E (1), we synthesized hederacolchiside E for the first time along with eleven of its derivatives. The neuroprotective effects of these compounds were further evaluated agains

Reengineering Chemical Glycosylation: Direct, Metal-Free Anomeric O-Arylation of Unactivated Carbohydrates

To sustain innovation in glycobiology, effective routes to well-defined carbohydrate probes must be developed. For over a century, glycosylation has been dominated by the formation of the anomeric Csp3?O acetal junction in glycostructures. A dissociative mechanistic spectrum spanning SN1 and SN2 is frequently operational thereby reducing the efficiency. By reengineering this fundamental process, an orthogonal disconnection allows the acetal to be formed directly from the reducing sugar without the need for substrate pre-functionalisation. The use of stable aryliodonium salts facilitates a formal O?H functionalisation reaction. This allows lactols to undergo mild, metal-free O-arylation at ambient temperature. The efficiency of the transformation has been validated using a variety of pyranoside and furanoside monosaccharides in addition to biologically relevant di- and trisaccharides (up to 85 %). Fluorinated mechanistic probes that augment the anomeric effect were employed. It is envisaged that this strategy will prove expansive for the construction of complex acetals under substrate-based stereocontrol.

Conformational Distortion Using a Molecular Lever: Synthesis and Conformational Studies of Galactoside Derivatives

Novel bicyclic d-galactose derivatives containing a molecular lever were synthesized and their conformations studied by 1H-NMR and crystallography. Increasing the bulkiness in the alkylidene ring in combination with introducing bulky O-protective groups on the pyranoside ring, causes a ring flip from a 4C1 into the axial rich 1C4 conformation. With less bulky protective groups, the pyranoside ring resides in the 4C1 conformation despite distortion of the external alkylidene ring.