79549-73-8

Upstream product

• 4304-12-5 (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 83050-00-4 benzyl 2-O-acetyl-4,6-O-benzylidene-3-O-tosyl-β-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 10343-13-2 benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 86833-16-1 endo-1,2:4,6-di-O-benzylidene-α-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 100-51-6 benzyl alcohol 
• 3006-41-5 4,6-O-benzylidene-D-glucose 
• 34246-23-6 benzyl D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 100-39-0 benzyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 83049-98-3 2,4,6-tri-O-acetyl-3-O-tosyl-β-D-glucopyranosyl bromide 

Downstream Products

• 130610-56-9 benzyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 130610-63-8 benzyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 70144-60-4 benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 86420-81-7 benzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 130610-58-1 benzyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 130610-57-0 benzyl 3-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 83049-97-2 benzyl 4,6-O-benzylidene-2,3-di-O-ethyl-β-D-glucopyranoside 
• 82122-45-0 benzyl 4,6-O-benzylidene-2,3-di-O-propyl-β-D-glucopyranoside 
• 177567-39-4 benzyl 4,6-O-benzylidene-2,3-di-O-methyl-β-D-glucopyranoside 
• 183953-29-9 benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 259826-53-4 benzyl 4,6-O-benzylidene-2,3-di-O-benzoyl-β-D-glucopyranoside 
• 67831-41-8 benzyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 83050-03-7 benzyl 4-O-benzyl-3-deoxy-2-O-methyl-β-D-ribo-hexopyranoside 
• 83050-07-1 benzyl 6-O-benzyl-3-deoxy-2-O-methyl-β-D-ribo-hexopyranoside 

Relevant academic research and scientific papers

Total Synthesis of a Hyperbranched N-Linked Hexasaccharide Attached to ATCV-1 Major Capsid Protein without Precedent

The N-glycans attached to some chloroviruses comprise a hyperbranched core structure without precedent. We are interested in the chemical synthesis of the hexasaccharide attached to ATCV-1 (Acanthocystis turfacea Chlorella virus 1) for its distinct structure. After exploring four routes, the target hexasaccharide 2 was successfully synthesized for the first time in overall 10% yield over 8 steps from thioglycoside building blocks. This synthetic protocol is characterized by the three-component one-pot glycosylation and the regioselective glycosylation reactions. The disclosed synthetic approach to this new type of N-glycans will facilitate the in-depth understanding of their biological functions.

Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates

Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har

Synthesis of Bradyrhizose from d -Glucose

We describe the synthesis of the unusual bicyclic sugar bradyrhizose in 14 steps and a 6% overall yield from d-glucose. The synthesis involves the elaboration of a trans-fused carbocyclic ring onto the preexisting glucopyranose framework followed by adjus

Synthesis of the trisaccharide repeating unit of capsular polysaccharide from Klebsiella pneumoniae

The incidences of primary, pyrogenic liver abscess complicated by meningitis and septic endophthalmitis caused by Klebsiella pneumoniae has increased globally. Earlier studies have shown that the capsular polysaccharide (CPS) of Klebsiella pneumoniae plays an important role in the resistance to phagocytosis and related pathogenicity. The first chemical synthesis of the trisaccharide repeating unit of this CPS has been achieved via stereoselective glycosylation with orthogonal and appropriate protecting groups. A new method for the pyruvylation of trans diol was developed.

Chemical Approach to Positional Isomers of Glucose-Platinum Conjugates Reveals Specific Cancer Targeting through Glucose-Transporter-Mediated Uptake in Vitro and in Vivo

Glycoconjugation is a promising strategy for specific targeting of cancer. In this study, we investigated the effect of d-glucose substitution position on the biological activity of glucose-platinum conjugates (Glc-Pts). We synthesized and characterized all possible positional isomers (C1α, C1β, C2, C3, C4, and C6) of a Glc-Pt. The synthetic routes presented here could, in principle, be extended to prepare glucose conjugates with different active ingredients, other than platinum. The biological activities of the compounds were evaluated both in vitro and in vivo. We discovered that varying the position of substitution of d-glucose alters not only the cellular uptake and cytotoxicity profile but also the GLUT1 specificity of resulting glycoconjugates, where GLUT1 is glucose transporter 1. The C1α- and C2-substituted Glc-Pts (1α and 2) accumulate in cancer cells most efficiently compared to the others, whereas the C3-Glc-Pt (3) is taken up least efficiently. Compounds 1α and 2 are more potent compared to 3 in DU145 cells. The α- and β-anomers of the C1-Glc-Pt also differ significantly in their cellular uptake and activity profiles. No significant differences in uptake of the Glc-Pts were observed in non-cancerous RWPE2 cells. The GLUT1 specificity of the Glc-Pts was evaluated by determining the cellular uptake in the absence and in the presence of the GLUT1 inhibitor cytochalasin B, and by comparing their anticancer activity in DU145 cells and a GLUT1 knockdown cell line. The results reveal that C2-substituted Glc-Pt 2 has the highest GLUT1-specific internalization, which also reflects the best cancer-targeting ability. In a syngeneic breast cancer mouse model overexpressing GLUT1, compound 2 showed antitumor efficacy and selective uptake in tumors with no observable toxicity. This study thus reveals the synthesis of all positional isomers of d-glucose substitution for platinum warheads with detailed glycotargeting characterization in cancer.

TANNIN INHIBITORS OF HIV

The invention provides a method to prevent or treat HIV-infection with synthetic tannins, and pharmaceutical compositions comprising synthetic tannins.

Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity

A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cel

DISACCHARIDES

A disaccharide having the structure (Formula I), and a disaccharide having the structure (Formula II) exhibit immunomodulatory activity.

Synthesis of anomerically pure, furanose-free α-benzyl-2-amino-2- deoxy-D-altro- and D-manno-pyranosides and some of their derivatives

The anomerically pure benzyl α-d-glycoside of 2-amino-2-deoxy- mannopyranoside was synthesized from d-glucopyranose via 2-amino-2-deoxy-d- altrose intermediates. Unlike the direct synthesis from mannosamine in the literature, our method provides furanose-

TMSCl as a mild and effective source of acidic catalysis in Fischer glycosidation and use of propargyl glycoside for anomeric protection

Practical Fischer glycosidation was effected at room temperature or 60°C by using 5 to 10 equiv. of TMSCl. The anomeric propargyl group formed by this method was found to be a versatile new protecting group, being stable in neat TFA but readily cleaved by treatment with Co2(CO)8 and TFA in CH2Cl2 via the formation of an alkyne-Co complex.