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

General 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. (-)-4-epi-Shikimic acid has been studied for its potential use in the production of pharmaceuticals, as it is a precursor for the synthesis of the anti-influenza drug oseltamivir (Tamiflu). Its unique stereochemical properties make it a valuable compound for the development of new drugs and chemical synthesis processes.

Upstream product

• 88517-54-8 (1S,2S,6R,7R)-4,4-Dimethyl-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid methyl ester 
• 17791-32-1 7-Oxabicyclo<2.2.1>hept-5-en-2-carbonsaeure-methylester 
• 88517-53-7 cis-exo-2,3-dihydroxy-6-methoxycarbonyl-7-oxabicycloheptane 
• 88165-26-8 (+/-)-3,4-O,O-isopropylidine-1-methoxycarbonyl-3α,4α,5α-trihydroxycyclohexene 
• 4372-89-8 (+/-)-methyl 5-epishikimate 
• 1476028-68-8 (3R,4S,5R)-ethyl 3,4-epoxy-5-hydroxycyclohex-1-ene-1-carboxylate 
• 261631-95-2 (-)-(1S)-1-{(4S,5S)-5-[(1S)-1-hydroxy-2-propenyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-propen-1-ol 
• 1121652-18-3 (3aS,5aS,6aS,6bS)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno-[2′,3′:3,4]benzo[1,2-d][1,3]dioxole 
• 1583240-50-9 (3aR,4S,5aR,6aR,6bS)-2,2-dimethylhexahydrooxireno[2′,3′:3,4]-benzo[1,2-d][1,3]dioxol-4-ol 
• 145107-27-3 (3aR,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno-[2′,3′:3,4]benzo[1,2-d][1,3]dioxole 
• 1582805-94-4 (1R,2R,3S,4S)-1-chloro-2-acetoxy-3,4-(isopropylidenedioxy)-cyclohex-5-ene 
• 1224733-28-1 ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate 
• 104464-18-8 (3aR,7R,7aS)-methyl 7-hydroxy-2,2-dimethyl-3a,4,7,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 1582806-02-7 (3aR,5aR,6aR,6bR)-methyl 2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2′,3′:3,4]benzo[1,2-d][1,3]dioxole-5-carboxylate 

Downstream Products

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

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

Sialyltransferase inhibitors based on CMP-quinic acid

Quinic acid was transformed into phosphitamides 16, 25, and 36, which could be readily linked to 5'-O-unprotected cytidine derivative 17. Ensuing oxidation of the obtained phosphite triesters with tBuO2H and hydrogenolytic de-O-benzylation furnished the corresponding phosphate diesters 18, 26, and 38. Base catalyzed removal of acetyl protecting groups, and methyl ester hydrolysis furnished CMP-Neu5Ac analogues 1d, 1e, and 2. Quinic acid was also transformed into 1,2-unsaturated diallyl α-hydroxymethyl-phosphate derivatives (R)- and (S)-46, which on reaction with cytidine phosphitamide 47 afforded the phosphite triesters. Subsequent oxidation with tBuO2H and then treatment with NEt3 gave phosphate diester derivatives (R)- and (S)-48. Deallylation, acetyl group removal, and methyl ester hydrolysis furnished (R)- and (S)-3, respectively. Treatment of (R)- and (S)-48 with DBU as a base led to acetic acid elimination, thus yielding, after de-O-allylation, acetyl group cleavage, and ester hydrolysis, diene derivative (E)-4. Donor substrate analogues 1d and 1e exhibited good α(2-6)-sialyltransferase inhibition (K(i): 2.0 · 10-4 and 2.0 · 10-5 M). However, transition state analogues (R)-, and particularly (S)-3 showed excellent inhibition properties (K(i): 1.6 · 10-6 and 2.7 · 10-7 M).