18933-68-1

Upstream product

• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 23339-18-6 methyl 2,3-dideoxy-α,β-D-erythro-hexopyranoside 
• 117468-12-9 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine 
• 2873-29-2 D-glucal triacetate 
• 634909-30-1 methyl 4,6-O-benzylidene-2,3-dideoxy-D-erythro-hexopyranoside 

Downstream Products

• 330953-54-3 (+)-[(2R,3S,6S)-2-cyanomethyl-6-methoxyoxan-3-yl] benzoate 
• 18933-69-2 methyl 4-O-benzoyl-2,3,6-trideoxy-α-D-erythro-hexopyranoside 
• 21317-50-0 methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside 
• 116490-64-3 2-Benzoyloxy-5-hydroxycyclohexanone 
• 330953-59-8 (+)-benzyl N-{2-[(2R,3S,6S)-6-methoxy-3-(tosyloxy)oxan-2-yl]ethyl}carbamate 
• 330953-62-3 (+)-benzyl N-{2-[(2R,3S,6S)-3-(imidazol-1-ylthiocarbonyloxy)-6-methoxyoxan-2-yl]ethyl}carbamate 
• 330953-55-4 (+)-benzyl N-{2-[(2R,3S,6S)-3-hydroxy-6-methoxyoxan-2-yl]ethyl}carbamate 
• 330953-63-4 (+)-benzyl N-{2-[(2S,6S)-6-methoxyoxan-2-yl]ethyl}carbamate 
• 330953-61-2 (+)-benzyl N-{2-[(2R,6S)-6-methoxy-5,6-dihydro-2H-pyran-2-yl]ethyl}carbamate 
• 393818-85-4 (+)-(2R,3S,6S)-2-{2-[2-(3,4-dichlorophenyl)acetylamino]ethyl}-6-methoxyoxan-3-yl 4-methylbenzenesulfonate 
• 393818-86-5 (+)-N-{2-[(2R,3R,6S)-3-azido-6-methoxyoxan-2-yl]ethyl}-2-(3,4-dichlorophenyl)acetamide 
• 393818-84-3 (+)-2-(3,4-dichlorophenyl)-N-{2-[(2R,3S,6S)-3-hydroxy-6-methoxyoxan-2-yl]ethyl}acetamide 
• 393818-89-8 (+)-1-[(1R,5R,6R)-6-azido-9-oxa-2-azabicyclo[3.3.1]nonan-2-yl]-2-(3,4-dichlorophenyl)ethan-1-one 
• 116490-60-9 Methyl 4-O-benzoyl-2,3,6-trideoxy-α-D-glycero-hex-5-enopyranoside 

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.

Synthesis and opioid-receptor binding of novel amino-substituted morphan analogues

Starting with methyl 4,6-O-benzylidene-α-D-glucopyranoside (4), an optimized procedure is reported for preparation of the bromide 7, which is transformed into the N-acylated heptopyranosamine 9. After introduction of an axially positioned azido moiety in