847984-56-9

Upstream product

• 69177-83-9 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-enofuranose 
• 86495-59-2 (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-eno-1,4-furanose 
• 64648-81-3 2-bromo-1,4-dimethoxynaphthalene 
• 847984-53-6 3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-1,2-O-isopropylidene-6-nitro-β-L-idofuranose 

Downstream Products

• 847984-58-1 (1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-1,2,4-trihydroxy-5-(1',4'-naphthoquinon-2'-yl)cyclohexane 
• 847984-57-0 (1R,2S,3S,4R,5S,6S)-6-amino-3-(benzyloxy)-5-(1',4'-dimethoxynaphthalen-2'-yl)cyclohexane-1,2,4-triol 

Relevant academic research and scientific papers

Preliminary studies on the incorporation of sugars into naphthoquinones: Synthesis of (1R,2S,3S,4R,4aS,11bS)-2-(benzyloxy)-1,2,3,4,4a,5-hexahydro-1,3,4- trihydroxy-11bH-benzo[b]carbazole-6,11-dione

The first total synthesis of (1R,2S,3S,4R,4aS,11bS)-2-(benzyloxy)-1,2,3,4, 4a,5-hexahydro-1,3,4-trihydroxy-11bH-benzo[b]carbazole-6,11-dione from D-glucose is described. The key steps of this synthesis are the stereoselective Michael addition of 2-lithium-1,4-dimethoxynaphthalene to 3-O-benzyl-5,6-dideoxy-1,2-O- isopropylidene-6-nitro-α-D-xilohex-5-enefuranose followed by the enantioselective intramolecular Henry reaction of 3-O-benzyl-5,6-dideoxy-5-C-(1, 4-dimethoxynaphthalene-2-yl)-6-nitro-β-l-idofuranose to the key (1R,2S,3S,4R,5S,6S)-3-(benzyloxy)-5-(1,4-dimethoxynaphthalene-2-yl)-1,2, 4-trihydroxy-6-nitrocyclohexane.

Studies on the Michael addition of naphthoquinones to sugar nitro olefins: First synthesis of polyhydroxylated hexahydro-11H-benzo[a]carbazole-5,6-diones and hexahydro-11bH-benzo[b]carbazole-6,11-diones

A strategy for the synthesis of the novel (6bR,7R,8S,9S,10S,10aR)-8- (benzyloxy)-7,9,10-trihydroxy-6b,7,8,9,10,10a-hexahydro-11H-benzo[a]carbazole-5, 6-dione is reported. The key steps were the Michael addition of 2-hydroxy-1,4-naphthoquinone to 1-nitrocy