80483-13-2

Upstream product

• 51921-33-6 1,2,3,4-tetra-O-acetyl-D-fucopyranose 
• 34371-41-0 1,2,3,4-tetra-O-acetyl-6-deoxy-β-D-galactopyranose 
• 7404-35-5 Acetic acid (3R,4R,5R,6S)-2,3,5-triacetoxy-6-methyl-tetrahydro-pyran-4-yl ester 
• 73-34-7 D-Fucose 
• 28915-80-2 2,3,4-tri-O-acetyl-L-fucopyranose 
• 30571-58-5 L-fucose tetraacetate 
• 73-34-7 6-deoxy-L-galactose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 506-96-7 Acetyl bromide 
• 73-34-7 6-deoxy-L-talopyranoe 
• 643-17-4 α-D-rhamnopyranose 
• 1187858-70-3 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 64-19-7 acetic acid 
• 4026-27-1 1,2:3,4-di-O-isopropylidene-α-D-fucopyranose 

Downstream Products

• 180471-90-3 8-methoxycarbonyloctyl 2,3,4-tri-O-acetyl-6-deoxy-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 27894-28-6 Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(6-benzoylamino-purin-9-yl)-6-methyl-tetrahydro-pyran-3-yl ester 
• 128473-05-2 dibenzyl 2,3,4-tri-O-acetyl-β-L-fucopyranosyl phosphate 
• 69558-02-7 Ethyl 2,3,4-tri-O-acetyl-1-thio-α/β-L-fucopyranoside 
• 3359-36-2 benzyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside 
• 84729-97-5 p-nitrophenyl 2,3,4-tri-O-acetyl-β-D-fucopyranoside 
• 1243575-77-0 C₄₀H₅₄O₁₃ 
• 77667-33-5 2-nitro-4-(4,4,5,5-tetramethylimidazolidin-2-yl 1-oxide)phenyl-2,3,4-tri-O-acetyl-β-D-fucopyranoside 
• 77667-36-8 2-nitro-4-(4,4,5,5-tetramethylimidazolin-2-yl 1-oxide)phenyl-β-D-fucopyranoside 
• 84730-04-1 p-nitrophenyl 2-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-β-D-fucopyranoside 
• 84730-05-2 p-nitrophenyl 2-O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-β-D-fucopyranoside 
• 84730-06-3 p-nitrophenyl 2-O-β-L-fucopyranosyl-β-D-fucopyranoside 
• 81329-62-6 p-nitrophenyl 2-O-α-L-fucopyranosyl-β-D-fucopyranoside 
• 84730-02-9 p-nitrophenyl 3,4-O-isopropylidene-2-O-(2,3,4-tri-O-acetyl-L-fucopyranosyl)-β-D-fucopyranoside 

Relevant academic research and scientific papers

Non-isosteric C-glycosyl analogues of natural nucleotide diphosphate sugars as glycosyltransferase inhibitors

A series of C-glycosyl ethylphosphonophosphate analogues of UDP-Glc, UDP-Gal, UDP-GlcNAc and GDP-Fuc were synthesized from the corresponding C-glycosyl ethylphosphonic acids. Analogues were obtained as α-anomers through either diastereoselective photo-induced radical addition of glycosyl bromides (d-Glc, d-Gal and l-Fuc) to diethyl vinylphosphonate, or a multi-step sequence (d-GlcNAc), with subsequent coupling with morpholidate-activated nucleotide monophosphates. The in vitro inhibitory activity of UDP-Gal, GDP-Fuc and UDP-GlcNAc analogues towards glycosyltransferases (β-1,4-GalT, FUT3 and LgtA) was evaluated through a competition fluorescence assay and IC50 values of 40 μM, 2 mM and 3.5 mM were obtained, respectively.

Synthesis of seleno-fucose compounds and their application to the X-ray structural determination of carbohydrate-lectin complexes using single/multi-wavelength anomalous dispersion phasing

Selenium-incorporated fucoses (seleno-fucoses) differing in the position of the seleno-substituent were synthesized and applied to the X-ray structural determination of a carbohydrate-lectin complex using single/multi-wavelength anomalous dispersion (SAD/

Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

Halogenation and anomerization of glycopyranoside by TESH/bromine and BHQ/bromine

Treatment of peracetylated glycosides and β-isopropyl glycosides with halogen in the presence of TESH and BHQ has been found to result in the halogenation and the anomerization, respectively. Peracetylatedglycosides treaded with I2/TESH or Br2/TESH leading tothe formation of corresponding glycosyl halides, and b-isopropyl glycosidesreacted with Br2/BHQ resulting in the formation of a-glycosides. The anomerizationof glycosidic bond was considered to be catalyzed by in situ formation of hydrogenbromide from the mixing of Br2/BHQ.

Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34

A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.

Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide

The first synthesis of the tetrasaccharide fragment of the anthracycline natural product Arugomycin is described. A reagent controlled dehydrative glycosylation method involving cyclopropenium activation was utilized to synthesize the α-linkages with complete anomeric selectivity. The synthesis was completed in 20 total steps, and in 2.5% overall yield with a longest linear sequence of 15 steps.

Neuroprotective activity of different monosaccharide-modified gastrodin analogs

Gastrodin is a very important and well-known bioactive glycoside compound in Chinese medicine. It is also known as a drug with neuroprotective function. Here, a practical diversified synthesis of a series of gastrodin analogs was reported, which involved four-step procedures consisting of bromination, oxidation, etherification, and reduction. Various gastrodin analogs were obtained in good yields. The compound 4c in this study has a good neuroprotective function: it can significantly downregulate tumor necrosis factor-α and inducible nitric oxide synthase protein levels. The results of this study can provide a research basis for the development of neuroprotective drugs.

Total Syntheses of Resin Glycosides Murucoidins IV and v

Murucoidins IV and V, two bioactive resin glycosides with complex yet similar structures isolated from the morning glory family, were synthesized in a convergent manner. All of the glycosylations in these syntheses including the key [3 + 2] coupling were

Direct and Regioselective Di-α-fucosylation on the Secondary Rim of β-Cyclodextrin

A straightforward glycosylation method is described to regio- and stereoselectively introduce two α-l-fucose moieties directly to the secondary rim of β-cyclodextrin. Using NMR and MS fragmentation studies, the nonasaccharide structure was determined, which was also visualized using molecular dynamics simulations. The reported glycosylation method proved to be robust on gram-scale, and may be generally applied to directly glycosylate β-cyclodextrins to make well-defined multivalent glycoclusters.

Synthesis of C3-Neoglycosides of digoxigenin and their anticancer activities

Cardiac glycosides exhibit significant anticancer effects and the glycosyl substitution at C3 position of digoxigenin is pivotal for their biological activity. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and explore more potent anticancer agents, a series of C3-O-neoglycosides and C3-MeON-neoglycosides of digoxigenin were synthesized by the Koenigs-Knorr and neoglycosylation method, respectively. In addition, digoxigenin bisdigitoxoside and monodigitoxoside were prepared from digoxin by sodium periodate (NaIO4) oxidation and 6-aminocaproic acid hydrolysis. The SAR analysis revealed that C3-O-neoglycosides of digoxigenin exhibited stronger cytotoxicity and induction of Nur77 expression of tumor cells than C3-MeON-neoglycosides. Also, 3β-O-glycosides exhibited stronger anticancer effects than 3α-O-glycosides. Among them, 3β-O-(β-L-fucopyranosyl)-digoxigenin (3i) showed the highest activity on induction of Nur77 expression and translocation from the nucleus to cytoplasm, leading to cancer cell apoptosis.