1309360-95-9

Upstream product

• 67-56-1 methanol 
• 1309360-93-7 CF₃O₃S^(1-)*C₃₇H₃₇O₈S⁽¹⁺⁾ 
• 1233488-80-6 ethyl 2-O-benzyl-3,4,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 173987-57-0 ethyl 2-O-benzyl-1-thio-β-D-glucopyranoside 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 174172-99-7 ethyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 
• 1309361-03-2 ethyl 2-O-benzyl-3,4,6-tri-O-benzoyl-1-thio-α-D-glucopyranoside 

Relevant academic research and scientific papers

Glycosidation of thioglycosides in the presence of bromine: Mechanism, reactivity, and stereoselectivity

Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that β-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, α-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into α-bromide that is totally unreactive under the established reaction conditions.

Direct synthesis of diastereomerically pure glycosyl sulfonium salts

It is reported that stable glycosyl sulfonium salts can be generated via direct anomeric S-methylation of ethylthioglycosides. Mechanistically, this pathway represents the first step in the activation of thioglycosides for glycosidation; however, it can f