897014-96-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
(-)-Methyl 4-epi-shikimate is used as a starting material for the synthesis of various pharmaceuticals and agrochemicals due to its unique structure and properties. Its presence in the shikimate pathway makes it a valuable compound for the development of new drugs and agrochemicals with potential applications in medicine and agriculture.
Used in Herbicide Development:
(-)-Methyl 4-epi-shikimate is used as a herbicide target for the development of new herbicides that can effectively control the growth of unwanted plants. Its role in the shikimate pathway makes it an attractive target for the design of herbicides that can selectively inhibit the growth of target plants without causing harm to non-target species.
Used in Aromatic Compound Production:
(-)-Methyl 4-epi-shikimate is used as an intermediate in the production of aromatic compounds, such as phenylpropanoids, lignin, and flavonoids. These compounds have various applications in the chemical, pharmaceutical, and agricultural industries, making (-)-methyl 4-epi-shikimate a valuable component in the synthesis of these important molecules.

Upstream product

• 1313032-29-9 (4R,5R,6R)-methyl 2-methylene-4,5,6-trihydroxyoct-7-enoate 
• 77-95-2 D-(-)-quinic acid 
• 186581-53-3 diazomethane 
• 21967-35-1 (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid 
• 273728-87-3 (1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester 
• 273728-71-5 (1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 1-methyl ester 
• 273728-74-8 Acetic acid (3aR,4R,5R,6R,7aR)-6-acetoxy-1,3-dioxo-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-octahydro-isobenzofuran-5-yl ester 
• 273728-68-0 (3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester 
• 273728-83-9 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3aR,4R,5R,6R,7aR)-5,6-dihydroxy-1,3-dioxo-octahydro-isobenzofuran-4-yloxy)-tetrahydro-pyran-3-yl ester 
• 97205-15-7 methyl 3,4-O-isopropylidene-5-oxoquinate 
• 97373-88-1 methyl (1R,3R,4S,5R)-1,5-dihydroxy-3,4-(isopropylidenedioxy)cyclohexane-1-carboxylate 
• 97205-16-8 methyl 4,5-O-isopropylidene-3-dehydro-4-epi-shikimate 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 901129-87-1 methyl 3-oxo-4-epi-shikimate 

Downstream Products

• 1101867-34-8 methyl (3R,4R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarboxylate 
• 1313032-32-4 (1S,2R,3S,4R,5R)-methyl 3,4,5-trihydroxy-2-((4-methoxybenzyl)thio)cyclohexanecarboxylate 
• 21967-35-1 (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid 
• 200636-42-6 (Z)-2-[(3R,4R,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-(3-tert-butyldimethylsilyloxypropoxy)-2-methylenecyclohexylidene]ethanol 
• 104528-69-0 methyl 3,4,5-tri-O-acetyl-4-epi-shikimate 

Relevant academic research and scientific papers

Glycomimetic building blocks: A divergent synthesis of epimers of shikimic acid

A divergent synthesis of (-)-4-epi-shikimic acid was developed. This route features a one-pot zinc-mediated reductive ring opening of an arabinofuranose followed by a Barbier reaction and culminates in a ring-closing metathesis. Functionalization of (-)-4

Novel and efficient syntheses of (-)-methyl 4-epi-shikimate and 4,5-epoxy-quinic and -shikimic acid derivatives as key precursors to prepare new analogues

We have developed simple methods that provide a rapid entry into the synthesis of a series of quinate and shikimate analogues, including (-)-methyl 4-epi-shikimate and the 4,5-epoxy analogues of the parent acids. Epoxy derivatives of quinic and shikimic a

Asymmetric synthesis of (-)-4-epi-shikimic acid

The major cycloadduct, arising from the Diels-Alder reaction of maleic anhydride and (1E)-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)buta- 1,3-diene, is converted into methyl 3-O-(β-D-glucopyranosyl)-4-epi-shikimate and into (-)-4-epi-shikimic acid in overall yields of 20 and 17% (based on the diene). (C) 2000 Elsevier Science Ltd.