102487-46-7

Upstream product

• 109-87-5 Dimethoxymethane 
• 102487-47-8 (E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate 
• 532-20-7 D-xylofuranose 
• 41341-99-5 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 16054-77-6 3,5-di-O-benzyl-D-xylofuranose 
• 100-44-7 benzyl chloride 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 50-00-0 formaldehyd 
• 87-72-9 D-(+)-xylose 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 102487-47-8 (E)-(4R,5S,6S)-5,7-Bis-benzyloxy-4,6-dihydroxy-hept-2-enoic acid methyl ester 
• 16054-77-6 3,5-di-O-benzyl-L-xylofuranose 
• 87-72-9 L-(-)-xylose 
• 114861-22-2 1,2-O-isopropylidene-α-L-xylofuranose 

Downstream Products

• 113473-80-6 4-((4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione 
• 85719-78-4 (+)-sesbanimide A 
• 102487-50-3 3-((4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-4-carbamoyl-butyric acid 
• 102487-49-0 3-((4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-pentanedioic acid 
• 108926-38-1 4-{(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-[1,3]dioxan-4-yl}-piperidine-2,6-dione 
• 85719-78-4 (-)-sesbanimide B 
• 102487-44-5 (4'S,5'R,6'R)-(+)-4-5'-benzyloxy-6'-benzyloxymethyl-1',3'-dioxan-4'-yl-2,6-piperidinedione 
• 102487-48-9 (4'S,5'R,6'R)-(-)-dimethyl 3-5'-benzyloxy-6'-benzyloxymethyl-1',3'-dioxan-4'-yl-glutarate 
• 102487-50-3 3-((4R,5S,6S)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-4-carbamoyl-butyric acid 
• 102487-49-0 3-((4R,5S,6S)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-pentanedioic acid 
• 102487-44-5 (4'R,5'S,6'S)-(-)-4-5'-benzyloxy-6'-benzyloxymethyl-1',3'-dioxan-4'-yl-2,6-piperidinedione 
• 102487-48-9 (4'R,5'S,6'S)-(+)-dimethyl 3-5'-benzyloxy-6'-benzyloxymethyl-1',3'-dioxan-4'-yl-glutarate 
• 102487-48-9 3-((4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-pentanedioic acid dimethyl ester 
• 126267-16-1 (1R,2S,6R,7R,9S)-(+)-9-(tert-butyldiphenylsilyloxy)-6-<(1S,2R)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2.7>tridecan-11-one 

Relevant academic research and scientific papers

An alternative synthesis of (+)-sesbanimide A

D-(+)-xylose has been converted to (+)-sesbanimide A in sixteen steps.The synthetic scheme involves an ususual tricyclic silylated derivative (9a) of the monobenzoylated product of the earlier described glutarimide intermediate (7).Compound 9a is a pivotal intermediate for the construction of ring C of (+)-sesbanimide A.

EFFICIENT SYNTHESIS AND ANTITUMOR ACTIVITY OF AN ENANTIOMERIC PAIR OF THE SESBANIMIDE AB-RING SYSTEMS

An enantiomeric pair of the fully unprotected AB-ring systems of sesbanimide A (1), a potent antitumor alkaloid, was efficiently synthesized from readily available D- and L-xylose.Examination on their in vitro antitumor activity clearly disclosed that the AB-ring system only made a small contribution to the notable cytotoxicity of 1.