18992-38-6

Upstream product

• 3615-41-6 L-Rhamnose 
• 108-24-7 acetic anhydride 
• 150-76-5 4-methoxy-phenol 
• 125520-01-6 ethyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 122089-71-8 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 
• 73-34-7 L-rhamnose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 42080-75-1 tris(4-methoxiphenyloxy)borane 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 406947-00-0 ethyl 2,3,4-tri-O-acetyl-S-(N-tosylimino)-1-thio-α-L-rhamnopyranoside 

Downstream Products

• 18918-36-0 4-methoxyphenyl α-L-rhamnopyranoside 
• 583041-06-9 4-methoxyphenyl 2-azido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 583041-07-0 4-methoxyphenyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranosyl-(1->3)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 583041-08-1 4-methoxyphenyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranosyl-(1->3)-4,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside 
• 583041-04-7 4-methoxyphenyl 4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 583041-05-8 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 583041-02-5 4-methoxyphenyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 583041-00-3 4-methoxyphenyl 4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 583041-01-4 4-methoxyphenyl 4-O-benzoyl-α-L-rhamnopyranoside 
• 583040-99-7 4-methoxyphenyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 870543-36-5 4-methoxyphenyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Revisit of the phenol O-glycosylation with glycosyl imidates, BF 3·OEt2 is a better catalyst than TMSOTf

With BF3·OEt2 as the catalyst, the glycosylation of phenols with glycosyl trichloroacetimidates (or N-phenyl trifluoroacetimidates) bearing 2-O-participating groups leads to the desired 1,2-trans-O-glycosides in generally excellent yields without formation of the 1,2-cis-anomers. However, with TMSOTf as the catalyst, the outcomes of the corresponding phenol O-glycosylation are highly dependent on the nucleophilicity of the phenols; less nucleophilic is the phenol, higher amounts of the 1,2-cis-O-glycoside together with more side-products are generated. 1,2-Orthoesters have been found to be the major products at a low temperature (a higher temperature. BF 3·OEt2 is an effective catalyst to promote the conversion of 1,2-orthoesters into the corresponding 1,2-trans-O-glycosides. However, the 1,2-orthoesters could be converted into the dioxolenium triflate and glycosyl triflate in the presence of TMSOTf, these intermediates which might be in equilibrium with the glycosyl oxocarbenium related species lead to the final mixture of the α/β-O-glycosides and side-products.

Efficient synthesis of a 6-deoxytalose tetrasaccharide related to the antigenic O-polysaccharide produced by Aggregatibacter actinomycetemcomitans serotype c

Concise synthesis of a 6-deoxy-α-l-talose tetrasaccharide, 6-deoxy-α-l-Talp-(1→3)-6-deoxy-α-l-Talp-(1→2)-6-deoxy-α-l-Talp-(1→3)-6-deoxy-α-l-Talp, the dimer of the disaccharide repeating unit of the OPS from Aggregatibacter actinomycetemcomitans serotype c

Using biological performance similarity to inform disaccharide library design

Designing better small-molecule discovery libraries requires having methods to assess the consequences of different synthesis decisions on the biological performance of resulting library members. Since we are particularly interested in how stereochemistry

Lanthanum trifluoromethane-sulfonate-catalyzed facile synthesis of per-O-acetylated sugars and their one-pot conversion to S-aryl and O-alkyl/aryl glycosides

Lanthanum trifluoromethanesulfonate-catalyzed solvent-free per-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.

ANTIBODIES FOR THE DETECTION OF BACILLUS ANTHRACIS AND VACCINE AGAINST B. ANTHRACIS INFECTIONS

35 Abstract The present invention relates to conjugates of oligosaccharides of formula 1, wherein R is a linker to a carrier protein and optionally comprises up to three further saccharides, 5 and which are useful for vaccination, methods of synthesis of

Total synthesis of antigen Bacillus anthracis tetrasaccharide - Creation of an anthrax vaccine candidate

Fighting Anthrax by recognizing its coat: The spores of Bacillus anthracis bear unique oligosaccharides on their surface for interaction with a host. These specific oligosaccharides may prove useful in the development of vaccines against this major biowar

Synthesis of anomeric sulfimides and their use as a new family of glycosyl donors

We introduce a convenient synthesis of anomeric sulfimides, the ability of which to act as glycosyl donors has been tested with various thiophilic reagents and acceptors.

The catalytic synthesis of aryl O-glycosides using triaryloxyboranes

Triaryloxyboranes worked as highly reactive glycosyl acceptors of glycosyl acetates to afford aryl O-glycosides in excellent yields. A catalytic amount of ytterbium(III) trifluoromethanesulfonate activated the formation reaction of aryl O-glycosidic linka