221012-72-2

Upstream product

• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 113893-72-4 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 
• 221002-70-6 methyl 2‐O‐benzoyl‐3‐O‐benzyl‐4,6‐O-benzylidene‐α‐D‐glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis and nmr characterisation of methyl mono- and DI-0-α-L-rhamnopyranosyl-α-d-glucopyranosiduronic acids

The synthesis and NMR characterisation of methyl mono- and di-O-α-L-rhamnopyranosyl-α-D-glucopyranosiduronic acids 1-6 are described. Two commercial starting products were used: methyl α-D-glucopyranoside 7 for the preparation of 1 and 2, and methyl (R)-4,6-O-benzylidene-α-D-glucopyranoside 8 for 3-6. Oxidation reaction of the hydroxymethyl group of glucose to a carboxylic acid group was performed by sodium hypochlorite 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)-mediated procedure after the coupling reaction. Glycosylation was carried out using the trichloroacetimidate approach with trimethylsilyl trifluoromethanesulfonate (TMSOTf) as promoter, resulting in a completely stereoselective formation of the a glycosyl linkage.