224044-69-3

Upstream product

• 224044-68-2 methyl (E)-4-oxo-4-<2-nitro-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate 
• 289665-42-5 3-(4-methoxy-4-oxobutanoyl)-2-nitrophenyl tetra-O-acetyl-β-D-glucopyranoside 
• 53055-05-3 3-methoxy 2-nitrobenzaldehyde 
• 103646-41-9 4-(3-methoxy-2-nitrophenyl)-4-oxobutanoic acid 
• 289665-38-9 1-(3-methoxy-2-nitrophenyl)-3-buten-1-ol 
• 289665-40-3 1-(3-methoxy-2-nitrophenyl)-1,4-butanediol 
• 289665-41-4 methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate 
• 224044-67-1 methyl (E)-4-oxo-4-(3-hydroxy-2-nitrophenyl)-2-butenoate 
• 93367-77-2 (E)-4-(3-hydroxy-2-nitrophenyl)-4-oxobut-2-enoic acid 

Downstream Products

• 156913-43-8 2-amino-3-(β-D-glucopyranosyloxy)-γ-oxobenzenebutanoic acid 

Relevant academic research and scientific papers

Total synthesis of α-deamino-3-(β-D-glucopyranosyloxy)kynurenine

α-Deamino-3-β-glucopyranosyloxy)kynurenine, a yellow, fluorescent compound isolated from human lens, was synthesized in 8 steps (10% overall yield) from commercially available 3-methoxy-2-nitrobenzaldehyde. Key events included preparation and glucosylatio

Synthesis of Human Ultraviolet Filter Compounds: O-β-D-Glucopyranosides of 3-Hydroxykynurenine and 2-Amino-3-hydroxy-γ-oxobenzenebutanoic Acid

The role of endogenous tryptophan-derived UV filters in aging lenses and in human cataract is becoming increasingly important. The two major UV filters found in the lenses of primates, the O-β-D-glucopyranosides of 3-hydroxykynurenine and 2-amino-3-hydroxy-γ-oxobenzenebutanoic acid, 1 and 2, were synthesized from the common benzoyl acrylate precursor 2-amino-3-hydroxybenzoyl-acrylic acid 10. Synthesis of compound 3, the α-N-acetyl derivative of 1, was achieved using coupling of 2-nitro-3-benzyloxyacetophenone 4 with the sodium salt of diethyl acetamidomalonate as a key step. This is the first reported synthesis of the lenticular glucopyranoside 2 and the N-acetyl compound 3.