36874-87-0

Upstream product

• 106-54-7 p-Chlorothiophenol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 19879-84-6 tetraacetyl thioglucose 
• 637-87-6 1-Chloro-4-iodobenzene 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 28217-44-9 p-chlorophenyl 1-thio-β-D-glucoside 
• 439-03-2 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 

Relevant academic research and scientific papers

Electrochemical nickel-catalyzed Migita cross-coupling of 1-thiosugars with aryl, alkenyl and alkynyl bromides

Here we report a simple route towards the synthesis of thioglycosides, in which electrochemical cross-coupling is used to form a S-C glycosidic bond from protected and unprotected thiosugars with functionalized aryl bromides under base free conditions. The reaction manifold that we report here demonstrates the power of electrochemistry to access highly complex glycosides under mild conditions.

Synthesis of glycosyl sulfoximines by a highly chemo- And stereoselective NH- And O-transfer to thioglycosides

A synthesis of unprecedented and stable glycosyl sulfoximines is reported. The developed strategies represent the first example of highly stereoselective sulfoximine formation directly from thioglycosides. This synthetic protocol has been tested on severa

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.

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

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.

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.

Diastereoselective thioglycosylation of peracetylated glycosides catalyzed by in situ generated iron(III) iodide from elemental iodine and iron

A facile in situ preparation of Fe(III) iodide from cheap, abundant elemental iodine and iron metal served as an efficient catalyst for the thioglycosylation of peracetylated glycosides with various alkyl and aryl mercaptans. Due to neighboring participation, the anomerically pure β-thioglycosides were obtained in good to high yields with exclusive diastereocontrol.

Highly diastereoselective thioglycosylation of functionalized peracetylated glycosides catalyzed by MoO2Cl2

Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and β-(1→6)-S-linked-thiodisaccharide synthesis.

Preparation of 1-fluoroglycosides from 1-arylthio and 1-arylselenoglycosides using 4-methyl(difluoroiodo)benzene

Treatment of readily available thio- and selenoglycosides with the reagent 4-methyl(difluoroiodo)benzene leads to the formation of the corresponding fluoroglycosides in moderate to good yield.