116003-78-2

Upstream product

• 115945-97-6 methyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 115945-96-5 methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(N-imidazolylsulfonyl)-α-D-altropyranoside 
• 116003-77-1 2-azido-2-deoxy-4,6-O-(phenylmethylene)methyl-α-D-altropyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 129217-24-9 4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside 

Downstream Products

• 1644625-03-5 C₃₁H₄₀N₂O₉ 
• 1644625-04-6 C₃₂H₄₂N₂O₉ 
• 1644625-05-7 C₃₄H₃₈N₂O₉ 
• 1644625-06-8 C₃₅H₄₀N₂O₉ 
• 1644625-07-9 C₂₉H₃₆N₂O₉ 
• 1644625-08-0 C₂₈H₃₄N₂O₉ 
• 1644625-09-1 C₃₁H₄₀N₂O₉ 
• 1644625-10-4 C₃₄H₃₈N₂O₉ 
• 1644625-35-3 C₃₁H₄₀N₂O₈S 
• 1644625-36-4 C₃₂H₄₂N₂O₈S 
• 1644625-27-3 C₂₄H₃₆N₂O₈ 
• 1644625-37-5 C₃₄H₃₈N₂O₈S 
• 1644625-38-6 C₃₅H₄₀N₂O₈S 
• 1644625-39-7 C₂₉H₃₆N₂O₈S 

Relevant academic research and scientific papers

Synthesis of 1,2,3-triazolyl analog of Neisseria meningitidis A capsular polysaccharide

Towards constructing a stable, non-hydrolyzable linkage for Neisseria meningitidis type A (MenA) polysaccharide, the phosphate bridge of its (1→6)-linked 2-acetamido-2-deoxy-α-D-mannopyranosyl phosphate repeating unit was replaced by a triazolyl analog using Cu(I) catalyzed click reaction. The synthesis involved anomeric azidation of N-acetyl-D-mannosamine derivative from its acetate precursor using stoichiometric amount of FeCl3 and one-pot synthesis of precursors for di- and tri- triazolyl saccharides with an azidoethyl spacer at the reducing end for bioconjugation.

Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks

Reported herein is the synthesis of a number of building blocks of 2-amino-2-deoxy-D-mannose from common D-glucose precursors.

Carbohydrate-based N-heterocyclic carbenes for enantioselective catalysis

Versatile syntheses of C2-linked and C2-symmetric carbohydrate-based imidazol(in)ium salts from functionalised amino-carbohydrate derivatives are reported. The novel NHCs were ligated to [Rh(COD)Cl]2 and evaluated in Rh-catalysed asymmetric hydrosilylation of ketones with good yields and promising enantioselectivities.

Modular hydroxyamide and thioamide pyranoside-based ligand library from the sugar pool: New class of ligands for asymmetric transfer hydrogenation of ketones

A large library of pyranoside-based hydroxyamide and thioamide ligands has been synthesized for asymmetric transfer hydrogenation in an attempt to expand the scope of the substrates to cover a broader range of challenging heteroaromatic and aryl/fluoroalkyl ketones. These ligands have the advantage that they are prepared from commercial D-glucose, D-glucosamine and α-amino acids, inexpensive natural chiral feedstocks. By carefully selecting the ligand components (substituents/configurations at the amide/thioamide moiety, the position of amide/thioamide group and the configuration at C-2), we found that pyranoside-based thioamide ligands provided excellent enantioselectivities (in the best cases, ees of >99% were achieved) in a broad range of ketones, including the less studied heteroaromatics and challenging aryl/fluoroalkyls. Note that both enantiomers of the reduction products can be obtained with excellent enantioselectivities by simply changing the absolute configuration of the thioamide substituent.

Chemoenzymatic synthesis of CMP-N-acetyl-7-fluoro-7-deoxy-neuraminic acid

7-Fluoro sialic acid was prepared and activated as cytidine monophosphate (CMP) ester. The synthesis started with d-glucose, which was efficiently converted into N-acetyl-4-fluoro-4-deoxy-d-mannosamine. Aldolase catalyzed transformation yielded the corres

Chemoenzymatic synthesis of GDP-azidodeoxymannoses: Non-radioactive probes for mannosyltransferase activity

GDP-2-, 3-, 4- or 6-azidomannoses can be successfully prepared from the corresponding azidomannose-1-phosphates and GTP using the enzyme GDP-Mannosepyrophosphorylase (GDP-ManPP) from Salmonella enterica and may serve as useful probes for mannosyltransferase activity. The Royal Society of Chemistry.

A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-d-mannopyranosides

4-Nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α- and β-d-mannopyranosides were prepared from methyl 4,6-O-benzylidene-α-d- glucopyranoside and 1,3,4,6-tetra-O-acetyl-α-d-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-α-d- and -β-d-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-α-d- mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-β-d-mannopyranoside in 20% and 44% overall yields, respectively.

Reactions of Some Pyranoside Diol Monotriflates with Nucleophiles and Bases

Reaction of pyranoside diol (equatorial) monotriflates with soft, nonbasic nucleophiles is a useful way to make axial heteroatom-substituted and "epimerized" pyranosides, particularly where a fused acetal ring inhibits ring contraction.Among the substrates examined (1,2,3,4,35), only 4 shows a strong tendency to give ring-contracted products.The reaction of 1-3 with more basic nucleophiles (F(1-), t-BuO(1-)) leads to the anhydrosugars 8, 25, and 26, respectively.The SN2 reaction of 35 with tetra n-butylammonium iodide forms the basis for a new synthesis of the Cerny epoxide 32.

SYNTHESIS OF A TRISACCHARIDE COMPONENT OF THE CAPSULAR POLYSACCHARIDE OF Streptococcus pneumoniae TYPE 19F

2-O--α,β-L-rhamnopyranose, a structural component of the capsular polysaccharide of Streptococcus pneumoniae type 19F, has been synthesized by sequential glycosylation reactions using the gl