158341-64-1

Basic information

• Product Name: (3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid
• Synonyms: (3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid
• CAS NO: 158341-64-1
• Molecular Weight: 174.153
• Mol File: 158341-64-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid(158341-64-1)
• EPA Substance Registry System: (3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid(158341-64-1)

Safety Data

• Hazardous Substances Data: 158341-64-1(Hazardous Substances Data)

Upstream product

• 1202183-68-3 (1S,2R,6S)-4-(ethoxycarbonyl)-6-(4-nitrobenzoyloxy)-cyclohex-3-ene-1,2-diyl diacetate 
• 136994-75-7 (E)-3-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-acrylic acid ethyl ester 
• 136994-76-8 2-(Diethoxy-phosphoryl)-3-((3aS,4R,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid ethyl ester 
• 102919-04-0 benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside 
• 136994-78-0 ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate 
• 158341-65-2 (3R,4S,5S)-5-acetoxy-3,4-(isopropylidenedioxy)cyclohex-1-enecarboxylic acid 
• 158227-61-3 Acetic acid (3aS,4S,7aR)-6-formyl-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester 
• 90927-40-5 (3R,4S,5S)-5-hydroxy-3,4-(isopropylidenedioxy)cyclohex-1-enecarboxylic acid 

Downstream Products

• 1132659-94-9 (3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 

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.

Enantiospecific synthesis of (-)-5-epi-shikimic acid and (-)-shikimic acid

Diastereoselective reaction of 2,3-O-isopropylidene-D-ribose with allylmagnesium chloride gave a 5 : 1 mixture of triols 4 and 5, which were then converted to nitrones 8 and 9. Intramolecular nitrone cycloaddition gave the isoxazolidines 10 and 11, which on acetylation gave the corresponding acetates 12 and 13 which were separated by repeated crystallisation. The major adduct 12 was converted to (-)-5-epi-shikimic acid 2. Reaction of the ribonolactone derivative 20 with allylmagnesium chloride gave the hemiacetal 21. Reduction of compound 21 with DIBAL afforded exclusively the diol 22, which was desilylated to give the triol 5. Similar chemistry to that employed for the synthesis of (-)-5-epi-shikimic acid 2 with the diol 5 resulted in the synthesis of (-)-shikimic acid 1.

Synthesis of shikimic acid and its phosphonate analogue via knoevenagel condensation

The Knoevenagel condensation and intramolecular olefination have been successfully exploited in a novel synthesis of shikimic acid 1 and its phosphonate analogue 2 from D-lyxose 5-aldehyde 7.