77-95-2

Basic information

• Product Name: Quinic acid
• Synonyms: (3R,5R)-1,3,4,5-TETRAHYDROXY-CYCLOHEXANECARBOXYLIC ACID;(-)-QUINIC ACID;QUINIC ACID;D-(−)-Quinic acid;(-) QUINIC ACID 500MG NEAT;(-)-QUINIC ACID FOR RESOLUTION OF RACEMATES 98+%;Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1.alpha.,3R,4.alpha.,5R)-;1,3,4,5-tetrahydroxy-(1α,3r,4α,5r)-cyclohexanecarboxylic acid
• CAS NO: 77-95-2
• Molecular Formula: C₇H₁₂O₆
• Molecular Weight: 192.17
• EINECS: 201-072-8
• Product Categories: chiral;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;Asymmetric Synthesis;Chiral Resolution Reagents;Chiral Resolving Reagents;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 77-95-2.mol
• Article Data: 26

Chemical Properties

• Melting Point: 165-170 °C
• Boiling Point: 248.13°C (rough estimate)
• Flash Point: 233.1 °C
• Appearance: White to very slightly yellow/Crystalline Powder
• Density: 1.64 g/cm3 (20℃)
• Vapor Pressure: 1.58E-09mmHg at 25°C
• Refractive Index: -43.5 ° (C=10, H2O)
• Storage Temp.: Store below +30°C.
• Solubility: 290g/l (experimental)
• PKA: 4.27±0.50(Predicted)
• Water Solubility: 400 g/l (20 ºC)
• Merck: 14,8059
• BRN: 2212412
• CAS DataBase Reference: Quinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Quinic acid(77-95-2)
• EPA Substance Registry System: Quinic acid(77-95-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: GU8650000
• Hazardous Substances Data: 77-95-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 77-95-2 differently. You can refer to the following data:
1. D(-)-Quinic Acid is used in the synthesis of anti-influenza/anti-swine flu medication.
2. D-(-)-Quinic acid has been used as a standard to determine the composition of organic acids in bitter gentian teas and in developing cranberry fruit by HPLC. It may be used in the preparation of 3,4-O-isopropylidene-3(R),4(S)-dihydroxycyclohexanone.
3. These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

General Description

D-(-)-Quinic acid, a plant metabolite, is chiral building block used in multistep chemical synthesis of natural compounds.

Purification Methods

Quinic acid crystallises from H2O with m 174o, and from EtOH with m 168-169o. [McComsey & Maryanoff J Am Chem Soc 59 2652 1994, pK: Timberlake J Chem Soc 2795 1959, Anet & Reynolds Aust J Chem 8 282 1955, Beilstein 10 III 2407, 10 IV 2257.]

InChI:InChI=1/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4?,5-,7+/m1/s1

Synthetic route

methyl (-)-quinate (191916-39-9) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
With sodium hydroxide; water for 13h; Ambient temperature;	100%
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 5h;	90%
Multi-step reaction with 4 steps 1: triethylamine / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere 2: Dess-Martin periodane / dichloromethane / 20 °C 3: sodium tetrahydroborate / ethanol / 0.67 h / -30 °C 4: hydrogenchloride / water / 1 h View Scheme

Methyl (1S,3R,4R,5R)-3-<(tert-Butyl)dimethylsilyloxy>-1,4,5-trihydroxycyclohexane-1-carboxylate (135711-58-9) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
With potassium hydroxide; acetic acid In tetrahydrofuran; water 1) 1 h, 2) 15 h, r.t.;	90%

3-caffeoylquinic acid (202650-88-2) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
With methanol; sodium hydroxide at 60℃; for 4h;	88%
With 3percent HCl at 90℃; for 3h; Product distribution;
Multi-step reaction with 2 steps 1: palladium/charcoal; acetic acid / Hydrogenation 2: aqueous hydrochloric acid View Scheme

3-caffeoylquinic acid (202650-88-2) → caffeic acid (331-39-5) + D-(-)-quinic acid (77-95-2)

Conditions	Yield
bei der Alkalispaltung;

1,3-di-O-caffeoylquinic acid (212891-05-9) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
With sodium hydroxide
With barium dihydroxide

(1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid (25514-46-9) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
With sodium hydroxide
With hydrogenchloride

D-Glucose (2280-44-6) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
microbial construct AB2848aroD/pKD136/pTW8090A;	25 mmol
With Escherichia coli QP1.1; pKD12138; standard fermentation medium In water at 33 - 37℃; for 48h; pH=7.0;

3,5-dicaffeoylquinic acid (2450-53-5, 16758-05-7, 89919-61-9, 89919-62-0, 101222-97-3) → caffeic acid (331-39-5) + D-(-)-quinic acid (77-95-2)

Conditions	Yield
With water; unspecific esterase hydrolysis;
With water hydrolysis with unspecific esterase;

5-O-p-coumaroylquinic acid methyl ester (114687-85-3) → p-Coumaric Acid (7400-08-0) + D-(-)-quinic acid (77-95-2)

Conditions	Yield
With potassium hydroxide In ethanol for 1h; Heating;

3,5-di-O-galloyl quinic acid → D-(-)-quinic acid (77-95-2)

Conditions	Yield
With tannase In water at 37℃; for 6h;

herbacetin 7-O-(6''-quinylglucoside) → D-(-)-quinic acid (77-95-2) + herbacetin (527-95-7)

Conditions	Yield
With hydrogenchloride In water

hydrogen cyanide (74-90-8) + Acetic acid (2R,6R)-2,6-diacetoxy-4-methylene-cyclohexyl ester (34315-08-7) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
Multistep reaction;

D-Glucose (2280-44-6) → shikimic acid (138-59-0) + D-(-)-quinic acid (77-95-2) + (-)-3-dehydroshikimic acid (2922-42-1)

Conditions	Yield
With E. coli SP1.1; pKD12112 for 12h; Product distribution; var. time;
With air; Escherichia coli SP1.1PTS-; pSC6.090B at 33℃; for 60h; pH=7;
With air; Escherichia coli SP1.1PTS-; pSC6.090B at 33℃; for 30h; pH=7;

5-dihydro-quinic acid → D-(-)-quinic acid (77-95-2)

Conditions	Yield
With ethanol; platinum Hydrogenation;

D-Glucose (2280-44-6) + phosphoenolpyruvic acid (138-08-9) → shikimic acid (138-59-0) + D-(-)-quinic acid (77-95-2) + (-)-3-dehydroshikimic acid (2922-42-1)

Conditions	Yield
With dipotassium hydrogenphosphate; E. coli SP1.1; pKD12138; citric acid In water at 33℃; pH=7.0; Enzyme kinetics; Further Variations:; Reagents;

(-)-(1S,4R,4aS,5R,8aR)-5-tert-Butyldimethylsilyloxy-1,4,4a,6,7,8a-hexahydro-endo-1,4-methanonaphthalen-8(5H)-one (171824-23-0) → D-(-)-quinic acid (77-95-2)

Conditions

Yield

Multi-step reaction with 11 steps 1: 86 percent / NaH / tetrahydrofuran / 23 h / Ambient temperature 2: 90 percent / O2, KF, P(OEt)3 / dimethylsulfoxide / 22 h / Ambient temperature 3: 100 percent / pyridine / 38 h / Ambient temperature 4: 100 percent / diphenyl ether / 1 h / 280 °C 5: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C 6: PPTS / 65 h 7: NaBH4 / methanol / 1.5 h / -78 °C 8: 100 percent / 14 h / 50 °C 9: 80 percent / Bu3SnH / toluene / 9 h / Heating 10: 86 percent / CBr4, MeOH / 19 h / Heating 11: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

(1R,4S,4aR,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-1,4,4a,7,8,8a-hexahydro-1,4-methano-naphthalene-6-carboxylic acid methyl ester (215929-06-9) → D-(-)-quinic acid (77-95-2)

Conditions

Yield

Multi-step reaction with 10 steps 1: 90 percent / O2, KF, P(OEt)3 / dimethylsulfoxide / 22 h / Ambient temperature 2: 100 percent / pyridine / 38 h / Ambient temperature 3: 100 percent / diphenyl ether / 1 h / 280 °C 4: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C 5: PPTS / 65 h 6: NaBH4 / methanol / 1.5 h / -78 °C 7: 100 percent / 14 h / 50 °C 8: 80 percent / Bu3SnH / toluene / 9 h / Heating 9: 86 percent / CBr4, MeOH / 19 h / Heating 10: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

(1R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enecarboxylic acid methyl ester (215929-09-2) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
Multi-step reaction with 7 steps 1: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C 2: PPTS / 65 h 3: NaBH4 / methanol / 1.5 h / -78 °C 4: 100 percent / 14 h / 50 °C 5: 80 percent / Bu3SnH / toluene / 9 h / Heating 6: 86 percent / CBr4, MeOH / 19 h / Heating 7: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

(1R,4S,4aR,6R,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-5-oxo-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalene-6-carboxylic acid methyl ester (215929-07-0) → D-(-)-quinic acid (77-95-2)

Conditions

Yield

Multi-step reaction with 9 steps 1: 100 percent / pyridine / 38 h / Ambient temperature 2: 100 percent / diphenyl ether / 1 h / 280 °C 3: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C 4: PPTS / 65 h 5: NaBH4 / methanol / 1.5 h / -78 °C 6: 100 percent / 14 h / 50 °C 7: 80 percent / Bu3SnH / toluene / 9 h / Heating 8: 86 percent / CBr4, MeOH / 19 h / Heating 9: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

(3aR,5S,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (215929-14-9) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / CBr4, MeOH / 19 h / Heating 2: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

(3aR,4S,5R,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (215929-12-7) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / 14 h / 50 °C 2: 80 percent / Bu3SnH / toluene / 9 h / Heating 3: 86 percent / CBr4, MeOH / 19 h / Heating 4: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

(3aS,5R,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-4-oxo-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (215929-11-6) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: NaBH4 / methanol / 1.5 h / -78 °C 2: 100 percent / 14 h / 50 °C 3: 80 percent / Bu3SnH / toluene / 9 h / Heating 4: 86 percent / CBr4, MeOH / 19 h / Heating 5: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

(1R,4S,4aR,6R,8R,8aS)-6-Acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-5-oxo-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalene-6-carboxylic acid methyl ester (215929-08-1) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / diphenyl ether / 1 h / 280 °C 2: 86 percent / OsO4, NMO, H2O / tetrahydrofuran / 72 h / 0 °C 3: PPTS / 65 h 4: NaBH4 / methanol / 1.5 h / -78 °C 5: 100 percent / 14 h / 50 °C 6: 80 percent / Bu3SnH / toluene / 9 h / Heating 7: 86 percent / CBr4, MeOH / 19 h / Heating 8: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

(3aS,4S,5R,7R,7aR)-5-Acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-4-(imidazole-1-carbothioyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (215929-13-8) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / Bu3SnH / toluene / 9 h / Heating 2: 86 percent / CBr4, MeOH / 19 h / Heating 3: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

(1R,3S,4R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-2-oxo-cyclohexanecarboxylic acid methyl ester (215929-10-5) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: PPTS / 65 h 2: NaBH4 / methanol / 1.5 h / -78 °C 3: 100 percent / 14 h / 50 °C 4: 80 percent / Bu3SnH / toluene / 9 h / Heating 5: 86 percent / CBr4, MeOH / 19 h / Heating 6: 100 percent / NaOH, H2O / 13 h / Ambient temperature View Scheme

shikimic acid (138-59-0) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
Multi-step reaction with 7 steps 1: methanol; diethyl ether / -20 - -15 °C 2: 78 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 0 °C 3: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 18 h / Heating 4: 82 percent / Bu4NF / tetrahydrofuran / 0.03 h 5: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 6: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 7: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme
Multi-step reaction with 8 steps 1: methanol; diethyl ether / -20 - -15 °C 2: 83 percent / TsOH / CH2Cl2 / 1.5 h / Ambient temperature 3: 88 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 6 h / Ambient temperature 4: 70 percent / HCl / methanol; H2O / 0.25 h 5: 81 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 24 h / Ambient temperature 6: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 7: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 8: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme

methyl shikimate (40983-58-2) → D-(-)-quinic acid (77-95-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: 78 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 0 °C 2: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 18 h / Heating 3: 82 percent / Bu4NF / tetrahydrofuran / 0.03 h 4: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 5: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 6: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme
Multi-step reaction with 7 steps 1: 83 percent / TsOH / CH2Cl2 / 1.5 h / Ambient temperature 2: 88 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 6 h / Ambient temperature 3: 70 percent / HCl / methanol; H2O / 0.25 h 4: 81 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 24 h / Ambient temperature 5: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 6: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 7: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme

Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate (101906-39-2) → D-(-)-quinic acid (77-95-2)

Conditions

Yield

Multi-step reaction with 5 steps 1: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 18 h / Heating 2: 82 percent / Bu4NF / tetrahydrofuran / 0.03 h 3: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 4: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 5: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme

Methyl (3R,4S,5R)-5-Hydroxy-3,4-<(methoxymethylene)dioxy>cyclohex-1-ene-1-carboxylate (91758-24-6, 135711-52-3, 135711-63-6) → D-(-)-quinic acid (77-95-2)

Conditions

Yield

Multi-step reaction with 6 steps 1: 88 percent / Et3N, 4-(dimethylamino)pyridine / dimethylformamide / 6 h / Ambient temperature 2: 70 percent / HCl / methanol; H2O / 0.25 h 3: 81 percent / 3.0M t-BuOOH / VO(acac)2 / CH2Cl2; toluene / 24 h / Ambient temperature 4: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 5: 72 percent / H2 / Raney-Ni / ethyl acetate / 3420 Torr 6: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H2O / 1) 1 h, 2) 15 h, r.t. View Scheme

D-(-)-quinic acid (77-95-2) → 1,5-quinide (665-27-0)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 24h; Heating;	100%
With Amberlyst (R) 15 ion-exchange resin In N,N-dimethyl-formamide; benzene for 16h; Heating;	99%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene for 12h; Reflux;	99%

methanol (67-56-1) + D-(-)-quinic acid (77-95-2) → methyl (-)-quinate (191916-39-9)

Conditions	Yield
With Amberlite IR 120 for 7h; Heating;	100%
With sulfuric acid at 20℃;	100%
With hydrogenchloride at 60℃; for 6h;	100%

D-(-)-quinic acid (77-95-2) + acetone (67-64-1) → (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2)

Conditions	Yield
With sulfuric acid; sodium sulfate for 1h; Heating;	100%
With toluene-4-sulfonic acid; 2,2-dimethoxy-propane	94%
With toluene-4-sulfonic acid at 56℃; for 48h; Molecular sieve;	93%

D-(-)-quinic acid (77-95-2) + dimethylglyoxal (431-03-8) + trimethyl orthoformate (149-73-5) → (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester (176798-26-8)

Conditions	Yield
With camphor-10-sulfonic acid In methanol for 16h; Heating;	99%
With camphor-10-sulfonic acid In methanol for 16h; Heating;	99%
With (1S)-10-camphorsulfonic acid In methanol for 19h; Reflux; Inert atmosphere;	99%

D-(-)-quinic acid (77-95-2) + cyclohexanone (108-94-1) → (-)-4,5-cyclohexylidenequinic acid lactone (35949-53-2)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 5h; Heating;	98%
With phosphoric acid for 0.75h; Heating;	87%
With sulfuric acid for 1h; Heating;	85%

D-(-)-quinic acid (77-95-2) + acetic anhydride (108-24-7) → (1R,3R,4R,5R)-(-)-quinic acid tetraacetate (32469-24-2)

Conditions	Yield
With dmap In pyridine for 24h; Ambient temperature;	98%
With pyridine Ambient temperature;	98%
With pyridine; dmap at 5℃; for 12h;	97%

D-(-)-quinic acid (77-95-2) + cyclohexanone (108-94-1) → C13H18O5

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 7h; Heating;	98%

D-(-)-quinic acid (77-95-2) + 2,2-dimethoxy-propane (77-76-9) → (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2)

Conditions	Yield
With toluene-4-sulfonic acid In acetone for 1h; Reflux;	98%
Stage #1: D-(-)-quinic acid With Amberlyst 15 In acetonitrile for 48h; Reflux; Inert atmosphere; Stage #2: 2,2-dimethoxy-propane In acetonitrile for 3h; Reflux; Inert atmosphere;	98%
With toluene-4-sulfonic acid In acetone for 7h; Reflux;	92%

D-(-)-quinic acid (77-95-2) + acetone (67-64-1) → C10H14O5

Conditions	Yield
With sulfuric acid at 100℃; for 0.0833333h; Microwave irradiation;	98%

D-(-)-quinic acid (77-95-2) + benzaldehyde (100-52-7) → (1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one (216662-57-6)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 19h; Heating;	97%
With toluene-4-sulfonic acid In toluene for 16h; Reflux;	92%
With toluene-4-sulfonic acid In toluene Heating;	84%

chloro-trimethyl-silane (75-77-4) + D-(-)-quinic acid (77-95-2) → Trimethylsilyltetra-O-trimethylsilylchinat (364628-95-5)

Conditions	Yield
With triethylamine at 0℃; for 4.5h;	95%

D-(-)-quinic acid (77-95-2) + pentan-3-one (96-22-0) → 3,4-O-ethylpropylidenequinic acid-1,5-lactone (374687-78-2)

Conditions	Yield
With phosphoric acid at 180℃; for 12h;	94%
With toluene-4-sulfonic acid In toluene for 5h; Heating;	68%
With phosphoric acid for 12h; Reflux;	25 %Chromat.

2,2-dimethylpropane (463-82-1) + D-(-)-quinic acid (77-95-2) → (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2)

Conditions	Yield
With toluene-4-sulfonic acid In ethyl acetate at 0 - 78℃; for 12h;	92%

N,N,N',N''-tetrahexyl-N'',N''-dimethylguanidinium chloride (672953-05-8) + D-(-)-quinic acid (77-95-2) → C7H11O6(1-)*C27H58N3(1+) (902493-71-4)

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane at 20℃; for 24h;	91%

D-(-)-quinic acid (77-95-2) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → (1R,3R,4R,5R)-(-)-quinic acid tetraacetate (32469-24-2)

Conditions	Yield
With perchloric acid at 20 - 60℃;	91%
With perchloric acid at 50 - 60℃; for 12h;

D-(-)-quinic acid (77-95-2) + benzaldehyde (100-52-7) → (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone (32384-44-4)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	90%
With toluene-4-sulfonic acid In benzene Heating; Inert atmosphere;	89%

D-(-)-quinic acid (77-95-2) + acetone (67-64-1) → 3,4-isopropylidenequinide (130474-38-3)

Conditions	Yield
With hydrogen cation for 16h; Ambient temperature;	90%
With hydrogen cation

D-(-)-quinic acid (77-95-2) → 3(R),5(R)-trihydroxycyclohexanone (95639-53-5)

Conditions	Yield
With oxygen; potassium hydroxide; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 20℃; for 18h; Sealed tube; Irradiation;	90%
With sulfuric acid In water at 20℃; for 3h;	76%
With sodium hypochlorite solution; sulfuric acid In water at 20℃; for 3h;	75%

methanol (67-56-1) + D-(-)-quinic acid (77-95-2) + dimethylglyoxal (431-03-8) + trimethyl orthoformate (149-73-5) → (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester (176798-26-8)

Conditions	Yield
With (1S)-10-camphorsulfonic acid for 24h; Reflux;	90%
With CSA	85%

D-(-)-quinic acid (77-95-2) + 6-Bromo-1-hexene (2695-47-8) → (3R,5R)-1,3,4,5-Tetrahydroxy-cyclohexanecarboxylic acid hex-5-enyl ester (855252-32-3)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 80℃; for 12h;	88%

D-(-)-quinic acid (77-95-2) → hydroquinone (123-31-9)

Conditions	Yield
With sodium hypochlorite; sulfuric acid for 10h; Heating;	87%

D-(-)-quinic acid (77-95-2) → (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2)

Conditions	Yield
	85%
With hydrogenchloride; acetone
With sulfuric acid; acetone

D-(-)-quinic acid (77-95-2) + benzaldehyde (100-52-7) → (3aR,5R,7R,7aS)-5,7-Dihydroxy-2-phenyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid (141171-64-4)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	85%
With toluene-4-sulfonic acid In benzene Heating;	85%

methanol (67-56-1) + D-(-)-quinic acid (77-95-2) + dimethylglyoxal (431-03-8) → (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester (176798-26-8)

Conditions	Yield
With camphor-10-sulfonic acid; trimethyl orthoformate Heating;	85%
With camphor-10-sulfonic acid; trimethyl orthoformate Heating;	79%

D-(-)-quinic acid (77-95-2) + 2-oxopropanal (78-98-8) + trimethyl orthoformate (149-73-5) → (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester (176798-26-8)

Conditions	Yield
With (1S)-10-camphorsulfonic acid In methanol	85%

dabigatran etexilate (211915-06-9) + D-(-)-quinic acid (77-95-2) → 3-(((2-(((4-(N'-hexyloxicarbonylcarbamidoyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)piridin-2-ylamino)propionic acid ethyl ester D-(-)-quinate

Conditions	Yield
In acetone at 20℃; for 4h;	84.7%

D-(-)-quinic acid (77-95-2) + 2,2-dimethoxy-propane (77-76-9) → 3,4-isopropylidenequinide (130474-38-3)

Conditions	Yield
Benzylsulfonic acid In benzene for 15h; Heating / reflux;	83.8%
With toluene-4-sulfonic acid In benzene for 18h; Heating;	18%
With toluene-4-sulfonic acid In acetone
In benzene Heating;

Upstream product

• 202650-88-2 3-caffeoylquinic acid 
• 212891-05-9 1,3-di-O-caffeoylquinic acid 
• 25514-46-9 (1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid 
• 2280-44-6 D-Glucose 
• 135711-58-9 Methyl (1S,3R,4R,5R)-3-<(tert-Butyl)dimethylsilyloxy>-1,4,5-trihydroxycyclohexane-1-carboxylate 
• 2450-53-5 3,5-dicaffeoylquinic acid 
• 114687-85-3 5-O-p-coumaroylquinic acid methyl ester 
• 74-90-8 hydrogen cyanide 
• 34315-08-7 Acetic acid (2R,6R)-2,6-diacetoxy-4-methylene-cyclohexyl ester 
• 191916-39-9 methyl (-)-quinate 
• 138-08-9 phosphoenolpyruvic acid 
• 171824-23-0 (-)-(1S,4R,4aS,5R,8aR)-5-tert-Butyldimethylsilyloxy-1,4,4a,6,7,8a-hexahydro-endo-1,4-methanonaphthalen-8(5H)-one 
• 215929-06-9 (1R,4S,4aR,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-1,4,4a,7,8,8a-hexahydro-1,4-methano-naphthalene-6-carboxylic acid methyl ester 
• 215929-09-2 (1R,5R)-1-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enecarboxylic acid methyl ester 

Downstream Products

• 99-50-3 3,4-Dihydroxybenzoic acid 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 10534-44-8 3-dehydroquinic acid 
• 2922-42-1 (-)-3-dehydroshikimic acid 
• 90-02-8 salicylaldehyde 
• 123-31-9 hydroquinone 
• 71-43-2 benzene 
• 108-95-2 phenol 
• 65-85-0 benzoic acid 
• 640-06-2 1,3,4-trihydroxy-6-oxa-bicyclo[3.2.1]octan-7-one 
• 665-27-0 1,5-quinide 
• 1768-31-6 pentachloroacetone 
• 81010-88-0 2,5-dihydroxy-benzene-1,3-disulfonic acid 
• 618-46-2 m-Chlorobenzoyl chloride 

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A new stereoselective synthesis of (-)-quinic acid from the naturally abundant (-)-shikimic acid is described. Ethyl shikimate 2 was first prepared in 97% yield via esterification of (-)-shikimic acid according to a previous report. Ester 2 was then transformed into an epimeric mixture of 3,4-O-benzylidene shikimate 3, which was directly converted into compound 4 in 90% yield (over 2 steps from ester 2) via an NBS-mediated acetal ring-opening reaction. Acetylization of the hydroxyl group at the C-5 position of compound 4 gave compound 5 in 98% yield. Compound 5 was transformed into compound 6 in 91% yield via a highly stereoselective Ru-catalyzed dihydroxylation. Subsequently, compound 6 was converted into epoxide 7 in 82% yield via an intramolecular SN2 type substitution. A regioselective epoxide-opening of compound 7 by PPh3-I2 complex furnished an iodo compound 8 in 79% yield. Removal of the iodine atom in compound 8 by Pd/C-catalyzed hydrogenation produced compound 9 in 92% yield. Methanolysis of compound 9 gave methyl quinate 10 in 92% yield. Finally, hydrolysis of compound 10 afforded the targeted compound (-)-quinic acid 1 in 90% yield. The title compound (-)-quinic acid 1 was stereoselectively synthesized through 10 steps starting from (-)-shikimic acid in 38% overall yield.