18933-69-2

Upstream product

• 18933-68-1 methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-erythrohexopyranoside 
• 634909-30-1 methyl 4,6-O-benzylidene-2,3-dideoxy-D-erythro-hexopyranoside 
• 2873-29-2 D-glucal triacetate 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 23339-18-6 methyl 2,3-dideoxy-α,β-D-erythro-hexopyranoside 

Downstream Products

• 634909-32-3 methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside 
• 21317-50-0 methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside 

Relevant academic research and scientific papers

Synthesis of the polyketomycin disaccharide

The disaccharide portion of the anthracycline antibiotic polyketomycin consists of the trideoxy sugar D-amicetose attached to the methyl-branched sugar L-axenose. The polyketomycin disaccharide was synthesized from methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside (methyl α-D-amicetoside) and phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-1-thio-α,β-L-xylo- hexopyranoside. The key coupling step was carried out by N-bromosuccinimide activation of the thioglycoside and gave the desired α (1→4) linked disaccharide exclusively in 71% yield, which was debenzylated by sodium and liquid ammonia.