68667-01-6

Upstream product

• 19879-84-6 tetraacetyl thioglucose 
• 350-46-9 4-Fluoronitrobenzene 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 636-98-6 p-nitrobenzene iodide 
• 586-78-7 para-nitrophenyl bromide 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 604-69-3 β-D-glucose pentaacetate 
• 1849-36-1 para-nitrobenzenethiol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 62205-46-3 p-N-acetamidophenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 36874-86-9 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-[(4-aminophenyl)thio]tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 2788-56-9 p-nitrophenyl 1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Ni/Photoredox-Dual-Catalyzed Functionalization of 1-Thiosugars

A general protocol for functionalization of glycosyl thiols has been reported. This protocol is based on a single-electron Ni/photoredox dual-catalyzed cross coupling between 1-thiosugars and a broad range of aryl bromides and iodides as well as alkenyl and alkynyl halides. This base-free method gives access to a series of functionalized thioglycosides in moderate to excellent yields with a perfect control of the anomeric configuration. Moreover, it has been shown that this methodology may be transposed successfully to the continuous-flow photoredox chemistry.

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.

Palladium-catalyzed cross-coupling reaction of thioglycosides with (hetero)aryl halides

α- and β-thioglycosides serve as effective nucleophiles for Buchwald-Hartwig cross-coupling reactions using functionalized (hetero)aryl halides. The functional group tolerance on the electrophilic partner is typically high, both benzyl and acetate protect

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.

Thio-arylglycosides with various aglycon para-substituents: A probe for studying chemical glycosylation reactions

Three series of thioglycosyl donors differing only in their respective aglycon substituents within each series have been prepared as representatives of typical glycosyl donors. The relative anomeric reactivities of these donors were quantified under compe

Odorless preparation of thioglycosides and Thio-Michael adducts of carbohydrate derivatives

A general, odorless, one-pot methodology has been developed for the preparation of 1,2-trans-thioglycosides and thio-Michael addition products of carbohydrate derivatives through triphenyl phosphine-mediated cleavage of disulfides and reaction of the thio

Formation and stability of oxocarbenium ions from glycosides

Structural, protecting group and leaving group effects in the formation of oxocarbenium intermediates were studied in the gas phase. It is found that significant stabilization of oxocarbenium cations is achieved by protecting groups that interact with the

Facile synthesis of 1,2-trans-nitrophenyl-1-thioglycopyranosides

1,2-trans-2-Nitro-, 4-nitro- and 2,4-dinitrophenyl-1-thioglycopyranosides were synthesized in high yield by condensation of per-O-acetyl-1-thioglucose with the appropriate nitro- or dinitrofluorobenzene in the presence of potassium carbonate. The pseudothiourea precursor was also used under these coupling conditions. 1,2-trans-4-Nitrophenyl-1-thioglycosides derived from β-D-galactose, β-D-xylose, α-L-arabinose and maltose were also obtained in good yield.