128775-56-4

Basic information

• Product Name: phenyl 3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside
• Synonyms: phenyl 3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside
• CAS NO: 128775-56-4
• Molecular Weight: 589.59
• Mol File: 128775-56-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: phenyl 3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside(128775-56-4)
• EPA Substance Registry System: phenyl 3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside(128775-56-4)

Safety Data

• Hazardous Substances Data: 128775-56-4(Hazardous Substances Data)

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 645-96-5 Benzeneselenol 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 1666-13-3 diphenyl diselenide 
• 29073-91-4 (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 
• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 158852-31-4 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 
• 135583-76-5 phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 

Downstream Products

• 128775-58-6 (2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(1-methoxy-allyloxy)-6-phenylselanyl-tetrahydro-pyran 
• 128775-66-6 (3R,3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-3-methyl-hexahydro-furo[3,2-b]pyran-2-one 
• 128775-67-7 (3S,3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-3-methyl-hexahydro-furo[3,2-b]pyran-2-one 
• 128775-68-8 [(R)-2-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methoxy-tetrahydro-pyran-2-yl)-propoxy]-tert-butyl-diphenyl-silane 
• 128775-57-5 ((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylselanyl-tetrahydro-pyran-3-yloxy)-methoxy-acetaldehyde 
• 150584-90-0 (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-3-ol 
• 384819-81-2 C₅₅H₆₀O₁₀ 
• 384819-83-4 C₅₅H₆₀O₁₀ 
• 455929-00-7 phenyl 2-O-(prop-1-enyl)-3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 

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.

Stereoselective synthesis of β-Phenylselenoglycosides from glycals and rationalization of the selenoglycosylation processes

β-Phenylselenoglycosides have been efficiently and stereoselectively synthesized by direct oxidative glycosylation of benzenselenolate (PhSe -) with glycals. A rationalization of the presently described β-selectivity and the opposite α-selectivity reported by Danishefsky in the ring-opening of epoxy glycals with benzeneselenol (PhSeH) is proposed.

Synthesis of the C-glycosidic analogue of adenophostin A and its uracil congener as potential IP3 receptor ligands. Stereoselective construction of the C-glycosidic structure by a temporary silicon-tethered radical coupling reaction

Synthesis of the C-glycosidic analogue 9 of adenophostin A, a very potent IP3 receptor agonist, and its uracil congener 10 was achieved via a temporary silicon-tethered radical coupling reaction as the key step. Phenyl 3,4,6-tri-O-(p-methoxyben