330476-89-6

Upstream product

• 149650-51-1 phenyl 3,4,6-tri-O-methyl-1-thio-β-D-glucopyranoside 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 62327-60-0 phenyl 2,3,4,6-tetra-O-methyl-1-thio-β-D-glucopyranoside 
• 330476-88-5 3,4,6-tri-O-methyl-α-D-glucopyranose 1,2-(methyl orthoacetate) 
• 108-98-5 thiophenol 
• 64032-47-9 phenyl 2-O-acetyl-3,4,6-tri-O-methyl-1-thio-Β-D-glucopyranoside 

Downstream Products

• 16740-98-0 tri-O-methyl-D-glucal 

Relevant academic research and scientific papers

Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents

Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that und

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.