75336-83-3

Upstream product

• 108-24-7 acetic anhydride 
• 135041-33-7 methyl 3-O-benzyl-β-L-fucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 65529-46-6 Methyl exo-2,3-di-O-benzylidene-α-L-rhamnopyranoside 
• 65475-56-1 methyl 4-O-acetyl-exo-2,3-O-benzylidene-α-L-rhamnopyranoside 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 76520-79-1 methyl 4-O-acetyl-2,3-di-O-benzyl-α-L-rhamnopyranoside 
• 75336-79-7 methyl 2,3-di-O-benzyl-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Selective 3-O-allylation and 3-O-benzylation of methyl α-D-manno-, α-L-rhamno- and β-L-fuco-pyranoside

The selective 3-O-allylation or 3-O-benzylation of methyl glycosides is a very useful procedure in anhydro sugar synthesis and oligosaccharide synthesis, because it can substantially simplify the reaction pathways. The 'direct stannylation method'3, by which unprotected glycopyranosides were treated with dibutyltin oxide and then alkylated, was effective for the 3-O-allylation of methyl α- (ref. 1) and β-D-galactopyranoside, but 'gave a quantitative recovery of starting material' in the case of methyl α-D-mannopyranoside. We report here a slightly modified procedure for direct stannylation that successfully accomplishes the 3-O-allylation and 3-O-benzylation of methyl α-D-manno-, α-L-rhamno- and β-L-fuco-pyranoside.