282088-45-3

Basic information

• Product Name: phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-α-D-mannopyranoside
• Synonyms: phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-α-D-mannopyranoside
• CAS NO: 282088-45-3
• Molecular Weight: 487.365
• Mol File: 282088-45-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-α-D-mannopyranoside(282088-45-3)
• EPA Substance Registry System: phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-α-D-mannopyranoside(282088-45-3)

Safety Data

• Hazardous Substances Data: 282088-45-3(Hazardous Substances Data)

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.

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