21967-35-1

Basic information

• Product Name: (-)-4-epi-Shikimic acid
• Synonyms: (-)-4-epi-Shikimic acid;(3R)-3β,4α,5α-Trihydroxy-1-cyclohexene-1-carboxylic acid;Epishikimic acid
• CAS NO: 21967-35-1
• Molecular Formula: C₇H₁₀O₅
• Molecular Weight: 174.1513
• Mol File: 21967-35-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-4-epi-Shikimic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-4-epi-Shikimic acid(21967-35-1)
• EPA Substance Registry System: (-)-4-epi-Shikimic acid(21967-35-1)

Safety Data

• Hazardous Substances Data: 21967-35-1(Hazardous Substances Data)

Usage

Description

(-)-4-epi-Shikimic acid is a chemical compound that belongs to the shikimic acid family. It is a stereochemical isomer of the naturally occurring shikimic acid and is commonly found in plants. Shikimic acid and its derivatives are important intermediates in the biosynthesis of aromatic amino acids and many other compounds. Its unique stereochemical properties make it a valuable compound for the development of new drugs and chemical synthesis processes.
Used in Pharmaceutical Industry:
(-)-4-epi-Shikimic acid is used as a precursor for the synthesis of the anti-influenza drug oseltamivir (Tamiflu) for its potential use in the production of pharmaceuticals.
Used in Chemical Synthesis Processes:
(-)-4-epi-Shikimic acid is used as an intermediate for the development of new drugs and chemical synthesis processes due to its unique stereochemical properties.

Upstream product

• 94903-41-0 (-)-methyl 4,5-O-benzylidene-4-epi-shikimate 
• 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 
• 286956-62-5 methyl (3R,4R,5R)-3-O-benzoyl-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate 
• 123994-31-0 methyl (3S,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate 
• 286956-61-4 methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate 
• 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 
• 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 
• 273728-71-5 (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 
• 273728-87-3 (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 
• 32384-44-4 (1S,3R,5RS,7R,8R)-5-phenyl-10-oxo-4,6,9-trioxatricyclo<6.2.1^1,8.0^3,7>undecan-1-ol 
• 94843-95-5 (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol 
• 94843-96-6 (1S,4S,6R,8S)-4-(methoxycarbonyl)-2-oxo-8-phenyl-7,9-dioxabicyclo<4.3.0>nonan-4-ol 
• 94843-97-7 (1R,2R,6R,8S)-2-(benzoyloxy)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene 
• 77-95-2 (1R,3R,4S)-1,3,4,5-Tetrahydroxy-cyclohexanecarboxylic acid 

Downstream Products

• 897014-96-9 (-)-methyl 4-epi-shikimate 
• 286956-63-6 (3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid 
• 286956-65-8 (3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde 
• 286956-64-7 (3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxy-N-methoxy-N-methylcyclohex-1-ene-1-carboxamide 
• 286956-67-0 Acetic acid (1R,5R,6R)-5,6-diacetoxy-3-[(S)-(bis-allyloxy-phosphoryl)-hydroxy-methyl]-cyclohex-3-enyl ester 
• 286956-66-9 Acetic acid (1R,5R,6R)-5,6-diacetoxy-3-[(R)-(bis-allyloxy-phosphoryl)-hydroxy-methyl]-cyclohex-3-enyl ester 
• 104528-69-0 methyl 3,4,5-tri-O-acetyl-4-epi-shikimate 

Relevant articles and documents

Stereodivergent Syntheses of All Stereoisomers of (?)-Shikimic Acid: Development of a Chiral Pool for the Diverse Polyhydroxy-cyclohexenoid (or -cyclohexanoid) Bioactive Molecules

Novel stereodivergent total syntheses of all the seven stereoisomers of (?)-shikimic acid [(?)-SA 1] have been systematically performed. (+)-ent-SA ent-1 was synthesized from (?)-SA 1 via 9 steps in 31 % overall yield; (?)-3-epi-SA 2 was synthesized from (?)-SA 1 via 5 steps in 66 % overall yield; (+)-3-epi-ent-SA ent-2 was synthesized from (?)-SA 1 via 7 steps in 43 % overall yield; (?)-4-epi-SA 3 was synthesized from (?)-SA 1 via 11 steps in 32 % overall yield; (+)-4-epi-ent-SA ent-3 was synthesized from (?)-SA 1 via 7 steps in 42 % overall yield; (?)-5-epi-SA 4 was synthesized from (?)-SA 1 via 6 steps in 56 % overall yield; and (+)-5-epi-ent-SA ent-4 was synthesized from (?)-SA 1 via 12 steps in 29 % overall yield. The stereochemistry of all the above seven stereoisomers of (?)-SA 1 were further studied by two dimensional (2D) 1H NMR technique.

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.