96251-69-3

Upstream product

• 96283-93-1 [2,2-Bis-methoxycarbonyl-2-((3aS,4R,7aR)-6-methoxycarbonyl-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-ethyl]-trimethyl-ammonium; iodide 
• 96251-67-1 2-Dimethylaminomethyl-2-((3aS,4R,7aR)-6-methoxycarbonyl-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-malonic acid dimethyl ester 
• 96283-92-0 methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate 
• 88165-26-8 methyl 3,4-O-isopropylideneshikimate 
• 99655-79-5 methyl <(1R),1α,5β,6α>-5-<<1-(methoxycarbonyl)ethenyl>oxy>-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate 

Downstream Products

• 61414-72-0 (-)-5-enolpyruvylshikimic acid 
• 96251-72-8 (4aR,8R,8aS)-8-{Bis-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxy}-3-methylene-2-oxo-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 89771-75-5 5-enol-pyruvoylshikimate 3-phosphate (EPSP) 
• 96251-70-6 compound Z₁ 
• 5811-68-7 (-)-5-enolpyruvylshikimic acid 

Relevant academic research and scientific papers

Conversion of Shikimic Acid to 5-Enolpyruvylshikimate 3-Phosphate

The synthesis of (-)-5-enolpyruvylshikimate 3-phosphate (3), a principle metabolite in the shikimic acid pathway, has been accomplished in 22percent overall yield from the known acetonide 6.A key intermediate in the synthesis is diester 9.Direct cyclization of this material affords lactone 10 and distinguishes the three hydroxyl groups of the shikimate nucleus.The phosphate moiety is introduced efficiently with tetrabenzyl pyrophosphate, followed by deprotection with trimethylsilyl bromide. (-)-5-Enolpyruvylshikimic acid (4), a secondary metabolite in the shikimate/chlorismate pathway, is formed on hydrolysis of 9.

SHIKIMATE-DERIVED METABOLITES. 14. CHIRAL SYNTHESIS OF 5-ENOLPYRUVYL-SHIKIMATE-3-PHOSPHATE

The title compound, a key biosynthetic intermediate in the shikimate metabolic pathway, has been synthesized in good yield from (-)-shikimic acid (1)