48149-74-2

Upstream product

• 2280-44-6 D-Glucose 
• 107-18-6 allyl alcohol 
• 492-61-5 β-D-glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 34272-03-2 propargyl β-D-glucopyranoside 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 83-87-4 D-glucose pentaacetate 
• 10257-28-0 D-Galactose 
• 16754-50-0 triallyl orthoformate 
• 106-95-6 allyl bromide 
• 50-99-7 D-glucose 
• 492-62-6 alpha-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 20746-64-9 allyl (R)-4,6-O-benzylidene-β-D-gluco-pyranoside 
• 84276-56-2 allyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 83921-79-3 allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 6207-44-9 1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 84218-69-9 allyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 146773-64-0 allyl 2,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 63976-06-7 1,2,3,4,6-penta-O-allyl-β-D-glucopyranose 
• 121280-53-3 allyl 4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 
• 473553-41-2 allyl 2,3-di-O-benzyl-4,6-O-(2-naphthyl)methylene-β-D-glucopyranoside 
• 305791-05-3 (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 305791-07-5 (+)-1-O-[(2R,3S,4Z)-2-azido-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 193222-97-8 [(2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol 
• 193223-12-0 (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde 
• 193223-08-4 (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid 

Relevant academic research and scientific papers

Sulfuric acid immobilized on silica: an excellent catalyst for Fischer type glycosylation

Fischer glycosylation, a widely used technique for the preparation of simple alkyl or aryl glycosides, has a few drawbacks including the use of strong mineral acids, excess alcohols, high temperature and long reaction times. This manuscript highlights a modification using sulfuric acid immobilized on silica as catalyst for the preparation of glycosides from free sugars such as d-glucose, d-galactose, d-mannose, l-rhamnose, l-fucose, N-acetyl-d-glucosamine and d-maltose with a diverse range of alcohols to afford a series of useful sugar derivatives in good to excellent yields.

Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions

A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.

Synthesis of the hyper-branched core tetrasaccharide motif of chloroviruses

Chemical synthesis of complex oligosaccharides, especially those possessing hyper-branched structures with one or multiple 1,2-cisglycosidic bonds, is a challenging task. Complementary reactivity of glycosyl donors and acceptors and proper tuning of the s

Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog

A new family of chiral C2 symmetric tetraazamacrocycles, coined ISAC for IminoSugar Aza-Crown, incorporating two iminosugars adopting a 4C1 conformation is disclosed. Multinuclear NMR experiments on the corresponding Cdsu

A Synthetic Carbohydrate-Protein Conjugate Vaccine Candidate against Klebsiella pneumoniae Serotype K2

Klebsiella pneumoniae causes pneumonia and liver abscesses in humans worldwide and contains virulence factor capsular polysaccharides and lipopolysaccharides linked to the cell wall. Although capsular polysaccharides are good antigens for vaccine producti

Preparation method of fondaparinux sodium disaccharide intermediate

The invention discloses a preparation method of fondaparinux sodium disaccharide intermediate. 1-O-substituent sulfonyl-2,3-bis-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranose directly reacts with 1,6-dehydrated-2-deoxy-2-azido-3-O-acetyl-beta-D-glucopyranose to prepare the fondaparinux sodium disaccharide intermediate as shown in a formula I; and meanwhile, the fondaparinux sodium intermediate asshown in the formula I can be used as a raw material to synthesize fondaparinux sodium intermediate as shown in a formula IV. The preparation method is simple and small in steps, the yield is high, the atomic utilization rate is high, the three wastes are small, and the preparation method is suitable for industrial large-scale production. Please see the description for the formula.

Immunomodulating beta-1,6-D-glucans

This invention relates to modifications of β-1,6-D-glucans, e.g., structures according to Formula (I), and the ability of these compositions to modulate an immune response.

?-1,6-GLUCAN TRASTUZUMAB ANTIBODY CONJUGATES

The present invention encompasses embodiments in which trastuzumab or a related trastuzumab antibody is conjugated to β-1,6-glucan oligomers. Thus, the present invention includes, among other things, compositions including trastuzumab conjugated to one or

Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A

Gram-negative bacteria comprise the majority of microbes that cause infections that are resistant to pre-existing antibiotics. The complex cell wall architecture contributes to their ability to form biofilms, which are often implicated in hospital-acquired infections. Biofilms promote antibiotic resistance by enabling the bacteria to survive hostile environments such as UV radiation, pH shifts, and antibiotics. The outer membrane of Gram-negative bacteria contains lipopolysaccharide (LPS), which plays a role in adhesion to surfaces and formation of biofilms. The main focus of this work was the synthesis of a library of glycolipids designed to be simplified analogues of the Lipid A, the membrane embedded portion component of LPS, to be tested as substrates or inhibitors of Heptosyltransferase I (HepI or WaaC, a glycosyltransferase enzyme involved in the biosynthesis of LPS). Fourteen analogues were synthesized successfully and characterized. While these compounds were designed to function as nucleophilic substrates of HepI, they all demonstrated mild inhibition of HepI. Kinetic characterization of inhibition mechanism identified that the compounds exhibited uncompetitive and mixed inhibition of HepI. Since both uncompetitive and mixed inhibition result in the formation of an Enzyme-Substrate-inhibitor complex, molecular docking studies (using AutoDock Vina) were performed, to identify potential allosteric binding site for these compounds. The inhibitors were shown to bind to a pocket formed after undergoing a conformational change from an open to a closed active site state. Inhibition of HepI via an allosteric site suggest that disruption of protein dynamics might be a viable mechanism for the inhibition of HepI and potentially other enzymes of the GT-B structural class.

Glycosyl Aldehydes: New Scaffolds for the Synthesis of Neoglycoconjugates via Bioorthogonal Oxime Bond Formation

The straightforward preparation of glycosyl neoconjugates by oxime (or hydrazone) bond formation represents a key bioorthogonal tool in chemical biology. However, when this strategy is employed by reacting the reducing end of the glycan moiety, the configuration and the stereochemical information is lost due to partial (or complete) opening of the glycan cyclic hemiacetal and the formation of the corresponding opened tautomers. We have completed the synthesis of a library of glycosyl aldehydes to be used as scaffold for the synthesis of neoglycoconjugates via oxime bond formation. These glycosyl aldehydes constitute a simple and accessible alternative to avoid loss of chiral information when conjugating, by oxime (or hydrazone) bonds, the aldehyde functionality present at the reducing end of natural carbohydrates.