1632129-92-0

Upstream product

• 825-83-2 4-trifluoromethylbenzenethiol 
• 2873-29-2 D-glucal triacetate 
• 50-99-7 D-glucose 
• 1561023-48-0 sodium S-4-(trifluoromethyl)phenyl sulfothioate 
• 118356-98-2 4,6-di-O-acetyl-3-O-D-glucal 

Relevant academic research and scientific papers

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

Unsaturated thioglycoside compound as well as selective synthesis method and application thereof

The invention discloses a synthesis method for selectively synthesizing an alpha-thioglycoside compound as shown in a formula (II) and a beta-thioglycoside compound as shown in a formula (III), which comprises the following steps: in a reaction solvent, by taking triacetyl glucose alkene as a reaction raw material and organic thiosulfates with different substituent groups as a sulfur source, under the action of a metal palladium salt and a ligand, selectively synthesizing an alpha-thioglycoside compound (II) and a beta-thioglycoside compound (III). The synthesis method provided by the invention has the advantages of easily available and cheap raw materials, simple reaction operation, mild reaction conditions, high yield and excellent functional group tolerance. According to the invention, synthesis and modification of some complex molecules are realized, and an efficient method for selectively constructing the thioglycoside compound containing the unsaturated bond is provided for research of pharmaceutical chemistry.

Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-d-Mannopyranosyl Sulfones

An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and α-d-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access α-d-mannopyranosyl sulfones in good yields with high regioselectivity.

Zn(OTf)2-catalyzed glycosylation of glycals: Synthesis of 2,3-unsaturated glycosides via a Ferrier reaction

A mild, catalytic, and efficient protocol has been developed for the synthesis of 2,3-unsaturated glycosides or 'pseudo-glycals' using Zn(OTf) 2. Stereoselective glycosylation of glycal donor with various acceptors comprising of alcohols, phenols, thiols, and sugar aglycones proceeds smoothly to afford the corresponding 2,3-unsaturaed glycosides in good to excellent yields. Georg Thieme Verlag Stuttgart New York.

Copper(II) triflate as a mild and efficient catalyst for ferrier glycosylation: Synthesis of 2,3-unsaturated o -glycosides

Various acceptors including carbohydrates, amino acids, natural products, and hydroxylamine derivatives were coupled with 3,4,6-tri-O-acetyl-d-glucal in the presence of Cu(OTf)2 as catalyst. The protocol offers facile and efficient Ferrier glycosylation for the synthesis of 2,3-unsaturaed O-glycosides in good yields and high anomeric selectivity.