53319-04-3

Upstream product

• 17187-64-3 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl bromide 
• 132562-65-3 methyl-(tetra-O-acetyl-α-D-gulopyranoside) 
• 13121-61-4 tetra-O-acetyl-1,5-anhydro-D-mannitol 
• 82682-67-5 (2R,3R,4R,5R)-3,4,5-Tris-trimethylsilanyloxy-2-trimethylsilanyloxymethyl-tetrahydro-pyran 
• 69-65-8 mannitol 
• 15430-94-1 6-bromo-6-deoxy-D-mannitol 
• 7647-01-0 hydrogenchloride 
• 14218-12-3 1,5-Anhydro-tetra-O-benzoyl-D-mannitol 
• 292638-85-8 acrylic acid methyl ester 
• 13242-53-0 acetobromomannose 
• 1769-06-8 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-mannopyranoside 
• 57-50-1 Sucrose 
• 1438585-76-2 1,5-anhydro-2,3,4,6-tetra-O-allyl-D-mannitol 
• 55529-69-6 trimethylsilyl 2,3,4,6-tetra-O-trimethylsilyl-D-mannopyranoside 

Downstream Products

• 13121-61-4 tetra-O-acetyl-1,5-anhydro-D-mannitol 
• 89195-85-7 1,5-anhydro-4,6-O-benzylidene-3-deoxy-3-nitro-D-mannitol 
• 74720-63-1 1,5-anhydro-4,6-O-benzylidene-3-deoxy-3-nitro-D-glucitol 
• 89195-86-8 1,5-anhydro-4,6-O-benzylidene-3-deoxy-3-nitro-D-galactitol 
• 177696-59-2 (2R,3R,4R,5R)-3,4,5-Tris-benzyloxy-2-trityloxymethyl-tetrahydro-pyran 
• 13121-47-6 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-toluene-p-sulfonyl-D-glucitol 
• 23275-67-4 lyxo-[2]Hexosulose-bis-phenylhydrazon 
• 177553-27-4 (2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-trityloxymethyl-tetrahydro-pyran 
• 38982-71-7 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-trityl-D-glucitol 
• 88043-87-2 1,5-anhydro-4,6-di-O-benzoyl-D-galactitol 
• 74629-56-4 1,5-anhydro-3,4,6-tri-O-benzoyl-D-galactitol 
• 65371-05-3 1,5-anhydro-3,6-di-O-p-tolylsulfonyl-D-galactitol 
• 65371-03-1 1,5-anhydro-2,3,6-tri-O-p-tolylsulfonyl-D-galactitol 
• 65371-00-8 1,5-anhydro-2,3,4,6-tetra-O-p-tolylsulfonyl-D-galactitol 

Relevant academic research and scientific papers

A protecting group-free approach for synthesizingC-glycosides through glycosyl dithiocarbamates

The first protection/deprotection-free process for radicalC-glycosylation has been achieved through one-step preparable glycosyl dithiocarbamates (GDTCs). The Giese-type reaction and radical allylation of unprotected GDTCs were successfully performed to obtain the corresponding α-C-glycosides stereoselectively under mild reaction conditions.

A Potent Mimetic of the Siglec-8 Ligand 6’-Sulfo-Sialyl Lewisx

Siglecs are members of the immunoglobulin gene family containing sialic acid binding N-terminal domains. Among them, Siglec-8 is expressed on various cell types of the immune system such as eosinophils, mast cells and weakly on basophils. Cross-linking of Siglec-8 with monoclonal antibodies triggers apoptosis in eosinophils and inhibits degranulation of mast cells, making Siglec-8 a promising target for the treatment of eosinophil- and mast cell-associated diseases such as asthma. The tetrasaccharide 6’-sulfo-sialyl Lewisx has been identified as a specific Siglec-8 ligand in glycan array screening. Here, we describe an extended study enlightening the pharmacophores of 6’-sulfo-sialyl Lewisx and the successful development of a high-affinity mimetic. Retaining the neuraminic acid core, the introduction of a carbocyclic mimetic of the Gal moiety and a sulfonamide substituent in the 9-position gave a 20-fold improved binding affinity. Finally, the residence time, which usually is the Achilles tendon of carbohydrate/lectin interactions, could be improved.

Structure–Activity Relationship Study of a Potent α-Thrombin Binding Aptamer Incorporating Hexitol Nucleotides

The replacement of one or more nucleotide residues in the potent α-thrombin-binding aptamer NU172 with hexitol-based nucleotides has been devised to study the effect of these substitutions on the physicochemical and functional properties of the anticoagulant agent. The incorporation of single hexitol nucleotides at the T9 and G18 positions of NU172 substantially retained the physicochemical features of the parent oligonucleotide, as a result of the biomimetic properties of the hexitol backbone. Importantly, the NU172-TH9 mutant exhibited a higher binding affinity toward human α-thrombin than the native aptamer and an improved stability even after 24 h in 90 percent human serum, with a significant increase in the estimated half-life. The anticoagulant activity of the modified oligonucleotide was also found to be slightly preferable to NU172. Overall, these results confirm the potential of hexitol nucleotides as biomimetic agents, while laying the foundations for the development of NU172-inspired α-thrombin-binding aptamers.

Modulating Electrostatic Interactions in Ion Pair Intermediates To Alter Site Selectivity in the C?O Deoxygenation of Sugars

Controlling which products one can access from the predefined biomass-derived sugars is challenging. Changing from CH2Cl2 to the greener alternative toluene alters which C?O bonds in a sugar are cleaved by the tris(pentafluorophenyl)borane/HSiR3 catalyst system. This increases the diversity of high-value products that can be obtained through one-step, high-yielding, catalytic transformations of the mono-, di-, and oligosaccharides. Computational methods helped identify this non-intuitive outcome in low dielectric solvents to non-isotropic electrostatic enhancements in the key ion pair intermediates, which influence the reaction coordinate in the reactivity-/selectivity-determining step. Molecular-level models for these effects have far-reaching consequences in stereoselective ion pair catalysis.

Controlling Sugar Deoxygenation Products from Biomass by Choice of Fluoroarylborane Catalyst

The feedstocks from biomass are defined and limited by nature, but through the choice of catalyst, one may change the deoxygenation outcome. We report divergent but selective deoxygenation of sugars with triethylsilane (TESH) and two fluoroarylborane catalysts, B(C6F5)3 and B(3,5-CF3)2C6H3)3 (BAr3,5-CF3). To illustrate, persilylated 2-deoxyglucose shows exocyclic C-O bond cleavage/reduction with the less sterically congested BAr3,5-CF3, whereas endocyclic C-O bond cleavage/reduction predominates with the more Lewis acidic B(C6F5)3. Chiral furans and linear polyols can be selectively synthesized depending on the catalysts. Mechanistic studies demonstrate that the resting states of these catalysts are different.

Harnessing the reactivity of poly(methylhydrosiloxane) for the reduction and cyclization of biomass to high-value products

Poly(methylhydrosiloxane) (PMHS) has been examined for its ability to reduce and subsequently cyclize carbohydrate substrates using catalytic tris(pentafluorophenyl)borane (BCF). The work herein is the first reported example of the direct conversion of monosaccharides to 1,4-anhydro and 2,5-anhydro products utilizing a hydrosiloxane reducing agent. PMHS is produced from waste products of the silicone industry, making it a green alternative to traditional hydrosilane reducing agents. This work thus contributes to the goal of utilizing renewable feedstocks in the production of fine-chemicals.

First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates

A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H3PO2-NaHCO3 system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.

Design and synthesis of boron containing monosaccharides by the hydroboration of D-glucal for use in boron neutron capture therapy (BNCT)

Boron neutron capture therapy (BNCT) is one of the radiotherapies that involves the use of boron-containing compounds for the treatment of cancer. Boron-10 (10B) containing compounds that can accumulate in tumor tissue are expected to be suitable agents for BNCT. We report herein on the design and synthesis of some new BNCT agents based on a D-glucose scaffold, since glycoconjugation has been recognized as a useful strategy for the specific targeting of tumors. To introduce a boryl group into a D-glucose scaffold, we focused on the hydroboration of D-glucal derivatives, which have a double bond between the C1 and C2 positions. It was hypothesized that a C–B bond could be introduced at the C2 position of D-glucose by the hydroboration of D-glucal derivatives and that the products could be stabilized by conversion to the corresponding boronic acid ester. To test this hypothesis, we prepared some 2-boryl-1,2-dideoxy-D-glucose derivatives as boron carriers and evaluated their cytotoxicity and cellular uptake activity to cancer cells, especially under hypoxic conditions.

Selective C?O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers’ Borane Generated In Situ

Described herein is the selective reduction of sugars with hydrosilanes catalyzed by using Piers’ borane [(C6F5)2BH] generated in situ. The hydrosilylative C?O bond cleavage of silyl-protected mono- and disaccharides in the presence of a (C6F5)2BH catalyst, generated in situ from (C6F5)2BOH, takes place with excellent chemo- and regioselectivities to provide a range of polyols. A study of the substituent effects of sugars on the catalytic activity and selectivity revealed that the steric environment around the anomeric carbon (C1) is crucial.

Isosorbide synthesis from cellulose with an efficient and recyclable ruthenium catalyst

Herein, we describe an efficient two-step pathway for isosorbide synthesis from cellulose with the use of new recyclable Ru-catalysts. We show that the oxidative and sulfonation treatments of the new Ru-catalysts increase the acidity and the hydrophilicity of the activated carbon support material, thus reducing the catalyst fouling caused by the build-up of insoluble products. Accordingly, the new Ru-catalysts are more resilient towards lignin containing cellulose than a commercial Ru/C catalyst, and the best Ru-catalyst maintains its high catalytic activity in four consecutive runs with dissolving pulp, microcrystalline cellulose and even with residual lignin containing bagasse pulp. Overall, our two-step approach provides isosorbide in high yields of 56-57 mol% (49-50 wt% of the substrate) from the cellulosic substrates.