106988-79-8

Upstream product

• 100-39-0 benzyl bromide 
• 80483-21-2 1,5-Anhydro-2,6-didesoxy-L-ribo-hex-1-enit 
• 106988-69-6 1,5-Anhydro-3-O-benzyl-2,6-didesoxy-L-ribo-hex-1-enit 
• 68673-58-5 (2S,3S)-3-hydroxy-2-methyl-2H-pyran-4(3H)-one 
• 106988-70-9 1,5-Anhydro-4-O-benzyl-2,6-dideoxy-L-ribo-hex-1-enitol 
• 117249-17-9 3,4-di-O-benzyl-L-rhamnal 
• 149561-65-9 (-)-(2S,3S)-3-(Benzyloxy)-2-methyl-2,3-dihydro-4H-pyran-4-one 
• 107079-29-8 1,5-Anhydro-3,4-di-O-benzoyl-2,6-didesoxy-L-ribo-hex-1-enit 

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.

Syntheses of Selectively Alkylated Enol Ethers in the L-ribo Series

The reduction of enulose 1a predominantly leads to L-digitoxal (3a), although this method presents a sluggish reaction with moderate yields.In contrast, the preparation from L-digitoxose (4a) in a three-step one-pot procedure represents an advantageous approach.Regioselective 3- or 4-O-alkylations are achieved by phase-transfer catalysis method or via stannylidene intermediates to give monosaccharide precursors of the L-ribo series valuable for further interglycosidic linking.