282088-45-3

Upstream product

• 83-87-4 D-Mannose pentaacetate 
• 1132-39-4 diphenylselenide 
• 1666-13-3 diphenyl diselenide 
• 13242-53-0 acetobromomannose 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 75996-25-7 Se-phenyl methaneselenosulfonate 
• 645-96-5 Benzeneselenol 

Downstream Products

• 189105-54-2 phenyl 1-seleno-α-D-mannopyranoside 
• 13121-61-4 tetra-O-acetyl-1,5-anhydro-D-mannitol 
• 492-93-3 1,5-anhydro-D-mannitol 
• 63554-21-2 (2R,4aR,8aR)-2-Phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 
• 539823-59-1 O²,O³;O⁴,O⁶-dibenzyliden-1,5-anhydro-mannitol 
• 536745-69-4 (2R,4aR,8aS)-8-Methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 221678-98-4 phenyl 2-O-benzyl-4,6-O-benzylidene-1-seleno-α-D-mannopyranoside 
• 282088-46-4 phenyl 4,6-O-benzylidene-1-seleno-α-D-mannopyranoside 
• 282088-47-5 phenyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-1-seleno-α-D-mannopyranoside 
• 270917-79-8 ethyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 282088-48-6 ethyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-3-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 282088-50-0 ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

Direct, stereoselective thioglycosylation enabled by an organophotoredox radical strategy

While strategies involving a 2e- transfer pathway have dictated glycosylation development, the direct glycosylation of readily accessible glycosyl donors as radical precursors is particularly appealing because of high radical anomeric selectivity and atom- and step-economy. However, the development of the radical process has been challenging owing to notorious competing reduction, elimination and/or SN side reactions of commonly used, labile glycosyl donors. Here we introduce an organophotocatalytic strategy through which glycosyl bromides can be efficiently converted into corresponding anomeric radicals by photoredox mediated HAT catalysis without a transition metal or a directing group and achieve highly anomeric selectivity. The power of this platform has been demonstrated by the mild reaction conditions enabling the synthesis of challenging α-1,2-cis-thioglycosides, the tolerance of various functional groups and the broad substrate scope for both common pentoses and hexoses. Furthermore, this general approach is compatible with both sp2 and sp3 sulfur electrophiles and late-stage glycodiversification for a total of 50 substrates probed.

InBr 3 -Catalyzed Synthesis of Aryl 1,2- trans -Thio(seleno)glycosides

InBr 3 is demonstrated to be an efficient catalyst for reactions of fully acetated aldoses with aryl mercaptans or selenophenol at room temperature, rapidly furnishing the corresponding thioglycosides or selenoglycosides with exclusively 1,2- t

Odorless eco-friendly synthesis of thio- and selenoglycosides in ionic liquid

An environmentally benign odorless methodology for the preparation of 1,2-trans-thio- and selenoglycosides is reported. In a one-pot condition, the reductive cleavage of disulfides and diselenides using triethylsilane and borontrifluoride diethyletherate combination followed by the reaction of the in situ generated thiolate and selenoetes with glycosyl acetate derivatives in recyclable room-temperature ionic liquid, [BMIM]BFresulted in excellent yields of thio- and selenoglycosides avoiding the use of obnoxious thiols/selenols and metallic catalysts.

Indium(I) iodide mediated efficient synthesis of selenoglycosides

A convenient odorless methodology has been developed for the preparation of selenoglycosides through indium(I) iodide mediated cleavage of diselenides and reaction with glycosyl bromides. The yields were excellent in all cases. Retention of the configurat

Synthesis of thio- and selenoglycosides by cleavage of dichalconides in the presence of zinc/zinc chloride and reaction with glycosyl bromides

A convenient odorless methodology has been devised for the preparation of 1,2-trans-thio- and selenoglycosides through zinc-mediated cleavage of disulfides and diselenides and reaction of the thiolate and selenides formed in situ with glycosyl bromides. T

Synthesis of galactofuranosyl-containing oligosaccharides corresponding to the glycosylinositolphospholipid of Trypanosoma cruzi.

The oligosaccharide beta-D-Galf-(1-->3)-alpha-D-Manp-(1-->2)-[beta-D-Galf- (1-->3)]-alpha-D-Manp-(1-->2)-alpha-D-Manp corresponds to the terminal end of the glycosylinositolphospholipid oligosaccharide of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease. Syntheses of methyl or ethylthio glycosides of the terminal disaccharide, trisaccharide, tetrasaccharide, and pentasaccharide corresponding to this structure are described. These syntheses employ the selective activation of a phenyl 1-selenogalactofuranoside or a phenyl 1-selenomannopyranoside donor over ethyl 1-thioglycoside acceptors with NIS-TfOH.