94160-77-7

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 

Downstream Products

• 94160-78-8 methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside 
• 1227925-11-2 bis(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranosid-2-yl)sulfane 
• 853943-20-1 methyl 2-S-acetyl-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-thio-α-D-mannopyranoside 
• 115945-98-7 acetyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-mannopyranoside 
• 1332832-44-6 methyl 3-O-benzyl-4-6-O-benzylidene-2-deoxy-2-fluoro-α-D-mannopyranoside 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 1332832-45-7 methyl 3-O-benzyl-2-deoxy-2-fluoro-α-D-mannopyranoside 
• 1332832-48-0 methyl 3-O-benzyl-2-deoxy-2-fluoro-6-O-pivaloyl-4-O-trifluoromethanesulfonyl-α-D-mannopyranoside 
• 1332832-49-1 methyl 3-O-benzyl-2,4-dideoxy-2,4-difluoro-6-O-pivaloyl-α-D-talopyranoside 
• 2774-19-8 (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 94119-07-0 (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester 
• 94119-08-1 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 94119-09-2 methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannopyranoside 
• 94119-06-9 (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane 

Relevant academic research and scientific papers

Efficient Two-Step Multifunctionalization of Substituted 2-Hydro-xyglycopyranosides

A straightforward route to diversely functionalized glycopyranosides is reported. 2,3-Enopyranosides, 2- and/or 3-azido-, 2-halopyranosides, and a hex-3-ulose, among other α- and β-glycopyranosides are easily obtained in good to excellent yields from 2-hydroxyglycopyranosides by means of a two-step process involving trifluoromethanesulfonation and subsequent treatment with the appropriate nucleophilic agent.

Synthesis and binding affinity analysis of α1-2- and α1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrene-mediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the α1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the α1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the α1-2-analog displayed very similar binding compared to the O-linked structure.

Facile synthesis of 4-deoxy-4-fluoro-α-d-talopyranoside, 4-deoxy-4-fluoro-α-d-idopyranoside and 2,4-dideoxy-2,4-difluoro-α-d- talopyranoside

The title compounds were prepared by two independent syntheses using inexpensive commercially available starting materials. 4-Deoxy-4-fluoro-α- d-talopyranoside served as a precursor to 4-deoxy-4-fluoro-α-d- idopyranoside, allowing for inversion of config

Non-glycosidically linked pseudodisaccharides: Thioethers, sulfoxides, sulfones, ethers, selenoethers, and their binding to lectins

Hydrolytically stable non-glycosidically linked tail-to-tail pseudodisaccharides are linked by a single bridging atom remote from the anomeric centre of the constituent monosaccharides. Some such pseudodisaccharides with sulfur or oxy gen bridges were found to act as disaccharide mimetics in their binding to the Banana Lectin and to Concanavalin A. A versatile synthetic route to a small library of such compounds is described.

Mannosazide methyl uronate donors. Glycosylating properties and use in the construction of β-ManNAcA-containing oligosaccharides

Mannosazide methyl uronate donors equipped with a variety of anomeric leaving groups (β- and α-S-phenyl, β- and α-N- phenyltrifluoroacetimidates, hydroxyl, β-sulfoxide, and (Rs)- and (Ss)-α-sulfoxides) were subjected to activating co

Synthesis of a trisaccharide and a tetrasaccharide from the cell-wall lipopolysaccharides of Azospirillum brasilense S17

A trisaccharide containing a D-mannosamine moiety and a tetrasaccharide containing an L-rhamnan chain that are found in the cell walls of Azospirillum brasilense S17 were synthesized concisely and in excellent yields. The key features of the synthetic str

SYNTHESES OF 1,5-DIDEOXY-1,5-IMINO-D-MANNITOL FROM D-MANNOSE AND D-GLUCOSE

Unambigous enantiospecific syntheses of 1,5-dideoxy-1,5-imino-D-mannitol (LU1, 1-deoxy-mannojirimycin) are reported (i) from D-mannose via hydrogenation of a 5-azido-5-deoxy mannose, and (ii) from D-glucose, in which the key step involves nucleophilic substitution of a trifluoromethanesulphonyl group from C-2 of D-glucose.