139903-49-4

Basic information

• Product Name: phenyl 2,3,4,6-tetra-O-benzyl-1-seleno-β-D-glycopyranoside
• Synonyms: phenyl 2,3,4,6-tetra-O-benzyl-1-seleno-β-D-glycopyranoside
• CAS NO: 139903-49-4
• Molecular Weight: 679.715
• Mol File: 139903-49-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: phenyl 2,3,4,6-tetra-O-benzyl-1-seleno-β-D-glycopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,3,4,6-tetra-O-benzyl-1-seleno-β-D-glycopyranoside(139903-49-4)
• EPA Substance Registry System: phenyl 2,3,4,6-tetra-O-benzyl-1-seleno-β-D-glycopyranoside(139903-49-4)

Safety Data

• Hazardous Substances Data: 139903-49-4(Hazardous Substances Data)

Upstream product

• 645-96-5 Benzeneselenol 
• 4981-97-9 phenyl 1-seleno-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 1666-13-3 diphenyl diselenide 
• 28622-58-4 phenyl selenosulfide 
• 2179-79-5 phenyl selenocyanate 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 23661-29-2 phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-glucopyranoside 
• 157896-05-4 Phenyl 2,3,4,6-tetra-O-benzoyl-1-seleno-β-D-glucopyranoside 
• 14262-85-2 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide 
• 4163-60-4 β-D-galactose peracetate 
• 154618-72-1 phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-galactopyranoside 
• 4981-97-9 phenyl 1-seleno-β-D-galactopyranoside 

Downstream Products

• 144069-06-7 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-galactopyranoside 
• 144069-05-6 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 154618-81-2 C₆₃H₆₈O₁₀S 
• 154618-80-1 C₆₃H₆₈O₁₀S 
• 61474-61-1 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-α-D-glucopyranoside 
• 84799-76-8 methyl O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 
• 132097-74-6 (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran 
• 132097-74-6 (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran 
• 1380505-22-5 (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran 
• 343565-52-6 (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran 
• 4981-97-9 phenyl 1-seleno-β-D-glucopyranoside 
• 1467598-18-0 diethyl (3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosid-2-ulosyl)malonate 

Relevant articles and documents

Catalytic and Photochemical Strategies to Stabilized Radicals Based on Anomeric Nucleophiles

Carbohydrates, one of the three primary macromolecules of living organisms, play significant roles in various biological processes such as intercellular communication, cell recognition, and immune activity. While the majority of established methods for the installation of carbohydrates through the anomeric carbon rely on nucleophilic displacement, anomeric radicals represent an attractive alternative because of their functional group compatibility and high anomeric selectivities. Herein, we demonstrate that anomeric nucleophiles such as C1 stannanes can be converted into anomeric radicals by merging Cu(I) catalysis with blue light irradiation to achieve highly stereoselective C(sp3)-S cross-coupling reactions. Mechanistic studies and DFT calculations revealed that the C-S bond-forming step occurs via the transfer of the anomeric radical directly to a sulfur electrophile bound to Cu(II) species. This pathway complements a radical chain observed for photochemical metal-free conditions where a disulfide initiator can be activated by a Lewis base additive. Both strategies utilize anomeric nucleophiles as efficient radical donors and achieve a switch from an ionic to a radical pathway. Taken together, the stability of glycosyl nucleophiles, a broad substrate scope, and high anomeric selectivities observed for the thermal and photochemical protocols make this novel C-S cross coupling a practical tool for late-stage glycodiversification of bioactive natural products and drug candidates.

Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite

A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-d-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.

Selective activation of glycosyl donors utilising electrochemical techniques: A study of the thermodynamic oxidation potentials of a range of chalcoglycosides

A series of six chalcoglycosides (phenyl-2,3,4,6-tetra-0-benzoyl-1-seleno-β-D-glucopyranoside, phenyl-2,3,4,6-tetraO-benzyl-1-seleno-β-D-glucopyranoside, phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside, p-tolyl-2,3,4,6-O-benzoyl-1-thio-β-D-glucop