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Upstream product

• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 55628-54-1 (2R,3S,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran 
• 62-53-3 aniline 
• 52485-06-0 3,4,6-tri-O-acetyl-D-glucal 
• 144071-49-8 1,2,3,4,6-penta-O-acetyl-D-allopyranose 
• 2595-05-3 Diacetone D-glucose 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 1141254-15-0 (2R,3R,6S)-3-(benzyloxy)-2-[(benzyloxy)methyl]-6-phenyldihydro-2H-pyran-4(3H)-one 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF 4 under mild conditions. This one-pot method stereospecifically provides α-and β-Aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.

Stereocontrolled Synthesis of 2-Deoxy- C-glycopyranosyl Arenes Using Glycals and Aromatic Amines

An efficient and stereoselective one-pot, two-step tandem α-arylation of glycals from readily available aryl amines via stable diazonium salts has been developed. Moreover, the stereoselective preparation of the challenging β-C-glycosyl arenes by the anomerization of α-C-glycosides using HBF4 is also described. This protocol has a broad substrate scope and a wide functional-group tolerance. It can be used for the gram-scale preparation of 3-oxo-C-glycosides, which are versatile substrates for the preparation of many biologically important C-glycosides.

ring opening-ring closure strategy for the synthesis of aryl-C-glycosides

A new ring-opening-ring closure strategy for the synthesis of aryl-C-glycosides was described. This strategy exploited the nickel-catalyzed regioselective β-O elimination of glycals by reactions with various aryl boronic acids or potassium aryltrifluoroborates to yield the ring-opened products, which underwent the Lewis acid, protonic acid, PhSeCl, or NBS mediated ring closure reactions to afford diverse aryl-C-glycosides. After Lewis acids and protonic acids were screened, it was found that, starting from the ring-opened substrates, the Ph3PHBr or Sc(OTf)3 mediated ring closure reaction provided α- or β-preferred aryl-C- Δ2,3-glycosides, respectively. Furthermore, β-d-phenyl-C-glycosides were successfully prepared via the PhSeCl-mediated cyclization reaction, whereas the α-d-phenyl-C-glycoside was obtained via the NBS-mediated cyclization reaction. After removal of the 2-substituted functionalities by Bu3SnH/AIBN, the synthesis of 2-deoxy-aryl-C- glycosides was ultimately realized in a stereoselective manner.