330476-84-1

Upstream product

• 168985-20-4 3,4,6-Tri-O-benzyl-β-D-glucopyranosyl 2-pyridyl sulfone 
• 127299-77-8 Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 208102-17-4 2-[(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine 
• 78-84-2 isobutyraldehyde 
• 330476-82-9 phenyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl sulfoxide 

Relevant academic research and scientific papers

Stereospecific synthesis of α- and β-C-glycosides from glycosyl sulfoxides: Scope and limitations

C-Glycosides derived from α-L-fuco-, α-D-gluco-, β-D-gluco-, and α-D-mannopyranose have been synthesized from the corresponding glycosyl phenyl sulfoxide through phenylsulfinyl-lithium exchange, to generate an anomeric carbanion, and subsequent reaction with a carbon electrophile. The reactions were stereospecific and proceeded with retention of the configuration at the anomeric center. Improved yields of C-glycosides were obtained by an inverse addition protocol. Trapping of the anomeric carbanion with aldehydes gave best results. Reaction with ketones, chloroformates, nitriles, and alkyl halides was also explored. Mechanistic aspects of the reaction are discussed.

A general approach to 1,2-trans-C-glycosides via glycosyl samarium(III) compounds

The samarium diiodide reduction of glycosyl pyridyl sulfones with ketones or aldehydes under Barbier conditions leads to the instantaneous and stereospecific formation of 1,2trans-C-glycosides in good to acceptable yields. Mannosyl pyridyl sulfones 5ac,h

Eine hoch stereoselektive Synthese von 1,2-trans-C-Glycosiden ueber Glycosylsamarium(III)-Verbindungen

Stichworte: Aldehyde * Asymmetrische Synthesen * C-Glycoside * Ketone * Samariumverbindungen