897014-96-9

Basic information

• Product Name: (-)-methyl 4-epi-shikimate
• Synonyms: (-)-methyl 4-epi-shikimate
• CAS NO: 897014-96-9
• Molecular Weight: 188.18
• Mol File: 897014-96-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (-)-methyl 4-epi-shikimate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-methyl 4-epi-shikimate(897014-96-9)
• EPA Substance Registry System: (-)-methyl 4-epi-shikimate(897014-96-9)

Safety Data

• Hazardous Substances Data: 897014-96-9(Hazardous Substances Data)

Usage

Description

(-)-Methyl 4-epi-shikimate is a significant chemical compound that plays a crucial role in the shikimate pathway, which is responsible for the biosynthesis of aromatic amino acids in plants, fungi, and bacteria. It serves as an important intermediate in the production of aromatic compounds, such as phenylpropanoids, lignin, and flavonoids. Furthermore, (-)-methyl 4-epi-shikimate has been explored for its potential use as a starting material for the synthesis of pharmaceuticals and agrochemicals. Its role as a herbicide target and its potential to inhibit the growth of unwanted plants has also been investigated.

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

• 186581-53-3 diazomethane 
• 21967-35-1 (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 901129-87-1 methyl 3-oxo-4-epi-shikimate 
• 1313032-29-9 (4R,5R,6R)-methyl 2-methylene-4,5,6-trihydroxyoct-7-enoate 
• 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 
• 77-95-2 D-(-)-quinic acid 

Downstream Products

• 104528-69-0 methyl 3,4,5-tri-O-acetyl-4-epi-shikimate 
• 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 

Relevant articles and documents

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

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.