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

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)

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 
• 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 
• 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 
• 94903-43-2 (1S,2S,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-en-2-ol 
• 1582805-99-9 (3aR,4S,5R,7aS)-methyl 4-hydroxy-2,2-dimethyl-3a,4,5,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 1582806-00-5 (3aR,4S,5S,5aR,6aR,6bS)-methyl 4-hydroxy-2,2-dimethylhexahydrooxireno[2′,3′:3,4]benzo[1,2-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 
• 104464-18-8 (3aR,7R,7aS)-methyl 7-hydroxy-2,2-dimethyl-3a,4,7,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 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 

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.

A C 2-symmetric chiral pool-based flexible strategy: Synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4- epi -shikimic acids, and (+)- and (-)-pinitol

Via combination of a novel acid-promoted rearrangement of acetal functionality with the controlled installation of the epoxide unit to create the pivotal epoxide intermediates in enantiomerically pure form, a simple, concise, flexible, and readily scalable enantiodivergent synthesis of (+)- and (-)-shikimic acids and (+)- and (-)-4-epi-shikimic acids has emerged. This simple strategy not only provides an efficient approach to shikimic acids but also can readily be adopted for the synthesis of (+)- and (-)-pinitols. These concise total syntheses exemplify the use of pivotal allylic epoxide 14 and its enantiomer ent-14. A readily available inexpensive C2-symmetric l-tartaric acid (7) served as key precursor. In general, the strategy here provides a neat example of the use of a four-carbon chiron and offers a good account of the synthesis of functionalized cyclohexane targets.

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.

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).

SHIKIMIC ACIDS FROM FURAN; METHODS OF STEREOCONTROLLED ACCESS TO 3,4,5-TRIOXIGENATED CYCLOHEXENES

Oxabicycloheptenes 1 and 2 are converted to 3,4,5-oxigenated cyclohexenes by stereocontrolled hydroxylations and epoxidations coupled with reverse-Michael cleavage of the oxabicyclo system.Three epimers of shikimic acid are synthesized by these methods.