97134-11-7

Basic information

• Product Name: Pinellic acid
• Synonyms: (9S,10E,12S,13S)-9,12,13-Trihydroxy-10-octadecenoic acid;(9S,11E,12S,13S)-9,12,13-Trihydroxy-10-octadecenoic acid;(9S,12S,13S,10E)-9,12,13-Trihydroxy-10-octadecenoic acid;Pinellic acid
• CAS NO: 97134-11-7
• Molecular Formula: C₁₈H₃₄O₅
• Molecular Weight: 330.45956
• Mol File: 97134-11-7.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pinellic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Pinellic acid(97134-11-7)
• EPA Substance Registry System: Pinellic acid(97134-11-7)

Safety Data

• Hazardous Substances Data: 97134-11-7(Hazardous Substances Data)

Usage

Description

Pinellic acid, a metabolite of linoleic acid, is a significant fatty acid found in lipids. It possesses properties as an adjuvant and an anti-inflammatory agent, making it a valuable compound in various applications.

Uses

Used in Pharmaceutical Industry:
Pinellic acid is used as an adjuvant for enhancing the effectiveness of vaccines and other immunotherapies. Its ability to stimulate the immune system and modulate immune responses contributes to its potential use in this application.
Used in Anti-Inflammatory Applications:
Pinellic acid is used as an anti-inflammatory agent to reduce inflammation and alleviate pain. Its role in modulating inflammatory processes makes it a promising candidate for the treatment of various inflammatory conditions.
Used in Cosmetic Industry:
Pinellic acid is used as an ingredient in cosmetic products for its anti-inflammatory and skin-soothing properties. It can help reduce redness, irritation, and inflammation, promoting healthier and more comfortable skin.
Used in Food Industry:
Pinellic acid is used as a natural preservative and antioxidant in the food industry. Its ability to prevent oxidation and spoilage helps maintain the quality and freshness of various food products.

Synthetic route

methyl (9S,10E,12S,13S)-9,12,13-trihydroxy-10-octadecenoate (93380-89-3) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Stage #1: methyl (9S,10E,12S,13S)-9,12,13-trihydroxy-10-octadecenoate With sodium hydroxide; water In methanol at 40℃; for 5h; Stage #2: With hydrogenchloride; water In methanol at 0℃;	85%

(9S,12S,13S)-(E)-9,12,13-trihydroxy-10-octadecenoic acid tert-butyl ester (401901-48-2) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 46h;	82%
With potassium hydroxide In ethanol; water at 20℃; for 46h;	82%

9(S)-hydroperoxyoctadeca-10Z,12E-dienoic acid (5502-91-0, 7324-20-1, 26911-36-4, 28396-96-5, 39692-45-0, 63121-49-3, 65941-74-4, 67597-24-4, 90760-93-3, 100018-30-2, 104759-96-8, 122046-44-0, 123410-63-9, 29774-12-7) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
With enzyme preparation from beetroot (Beta vulgaris spp. vulgaris var. vulgaris) at 23℃; for 1h; pH=6.7; aq. phosphate buffer; Enzymatic reaction; stereospecific reaction;	80%

(S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid (935746-75-1) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
With hydrogenchloride In methanol at 20℃;	78%
hydrogenchloride In methanol at 20℃;

(9S,10E)-11-[(4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl]-9-(methoxymethoxy)undec-10-enoic acid (1200721-24-9) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 10h;	66%

(S)-11-(4-methoxybenzyloxy)undec-1-yn-3-ol (935746-69-3) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 8 steps 1: 98 percent / imidazole / CH2Cl2 / 0 °C 2: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 3: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 4: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 5: 92 percent / TsOH / CH2Cl2 / 20 °C 6: IBX / ethyl acetate / 5 h / Heating 7: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 8: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 2.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 3.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 4.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 5.1: 92 percent / p-TSA / CH2Cl2 6.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 6.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 7.1: HCl / methanol / 20 °C View Scheme

(E)-ethyl 11-(4-methoxybenzyloxy)undec-2-enoate (935746-64-8) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 13 steps 1: 96 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 2: 94 percent / TsOH / CH2Cl2 / 20 °C 3: 95 percent / DIBAL-H / CH2Cl2; toluene / 2 h / 0 - 20 °C 4: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 5: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 6: 98 percent / imidazole / CH2Cl2 / 0 °C 7: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 8: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 9: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 10: 92 percent / TsOH / CH2Cl2 / 20 °C 11: IBX / ethyl acetate / 5 h / Heating 12: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 13: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 12 steps 1.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 2.1: 96 percent / p-TSA / CH2Cl2 3.1: 96 percent / DIBAL-H / CH2Cl2 / 2 h / 0 - 20 °C 4.1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 5.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 6.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 7.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 8.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 9.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 10.1: 92 percent / p-TSA / CH2Cl2 11.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 11.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 12.1: HCl / methanol / 20 °C View Scheme

((4S,5S)-5-(8-(4-methoxybenzyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol (935746-67-1) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 10 steps 1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 2: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 3: 98 percent / imidazole / CH2Cl2 / 0 °C 4: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 5: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 6: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 7: 92 percent / TsOH / CH2Cl2 / 20 °C 8: IBX / ethyl acetate / 5 h / Heating 9: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 10: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 9 steps 1.1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 2.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 3.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 4.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 5.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 6.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 7.1: 92 percent / p-TSA / CH2Cl2 8.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 8.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 9.1: HCl / methanol / 20 °C View Scheme

(4S,5R)-4-(8-(4-methoxybenzyloxy)octyl)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (935746-68-2) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 9 steps 1: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 2: 98 percent / imidazole / CH2Cl2 / 0 °C 3: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 4: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 5: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 6: 92 percent / TsOH / CH2Cl2 / 20 °C 7: IBX / ethyl acetate / 5 h / Heating 8: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 9: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 2.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 3.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 4.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 5.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 6.1: 92 percent / p-TSA / CH2Cl2 7.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 7.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 8.1: HCl / methanol / 20 °C View Scheme

(4R,5S)-ethyl 5-(8-(4-methoxybenzyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (935746-66-0) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 11 steps 1: 95 percent / DIBAL-H / CH2Cl2; toluene / 2 h / 0 - 20 °C 2: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 3: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 4: 98 percent / imidazole / CH2Cl2 / 0 °C 5: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 6: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 7: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 8: 92 percent / TsOH / CH2Cl2 / 20 °C 9: IBX / ethyl acetate / 5 h / Heating 10: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 11: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 10 steps 1.1: 96 percent / DIBAL-H / CH2Cl2 / 2 h / 0 - 20 °C 2.1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 3.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 4.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 5.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 6.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 7.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 8.1: 92 percent / p-TSA / CH2Cl2 9.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 9.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 10.1: HCl / methanol / 20 °C View Scheme

(2R,3S)-ethyl 11-(4-methoxybenzyloxy)-2,3-dihydroxyundecanoate (935746-65-9) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 12 steps 1: 94 percent / TsOH / CH2Cl2 / 20 °C 2: 95 percent / DIBAL-H / CH2Cl2; toluene / 2 h / 0 - 20 °C 3: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 4: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 5: 98 percent / imidazole / CH2Cl2 / 0 °C 6: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 7: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 8: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 9: 92 percent / TsOH / CH2Cl2 / 20 °C 10: IBX / ethyl acetate / 5 h / Heating 11: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 12: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 11 steps 1.1: 96 percent / p-TSA / CH2Cl2 2.1: 96 percent / DIBAL-H / CH2Cl2 / 2 h / 0 - 20 °C 3.1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 4.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 5.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 6.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 7.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 8.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 9.1: 92 percent / p-TSA / CH2Cl2 10.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 10.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 11.1: HCl / methanol / 20 °C View Scheme

((S)-11-(4-methoxybenzyloxy)undec-1-yn-3-yloxy)(tert-butyl)diphenylsilane (935746-70-6) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 7 steps 1: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 2: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 3: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 4: 92 percent / TsOH / CH2Cl2 / 20 °C 5: IBX / ethyl acetate / 5 h / Heating 6: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 7: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 2.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 3.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 4.1: 92 percent / p-TSA / CH2Cl2 5.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 5.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 6.1: HCl / methanol / 20 °C View Scheme

(9S,12S,13S,E)-9-(tert-butyldiphenylsilyloxy)-octadec-10-ene-1,12,13-triol (935746-73-9) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / TsOH / CH2Cl2 / 20 °C 2: IBX / ethyl acetate / 5 h / Heating 3: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 4: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: 92 percent / p-TSA / CH2Cl2 2.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 2.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 3.1: HCl / methanol / 20 °C View Scheme

(S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-en-1-ol (935746-74-0) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: IBX / ethyl acetate / 5 h / Heating 2: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 3: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 1.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 2.1: HCl / methanol / 20 °C View Scheme

((S,E)-1-(4-methoxybenzyloxy)octadec-12-en-10-yn-9-yloxy)(tert-butyl)diphenylsilane (935746-71-7) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 6 steps 1: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 2: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 3: 92 percent / TsOH / CH2Cl2 / 20 °C 4: IBX / ethyl acetate / 5 h / Heating 5: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 6: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 2.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 3.1: 92 percent / p-TSA / CH2Cl2 4.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 4.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 5.1: HCl / methanol / 20 °C View Scheme

(6S,7S,10S)-10-(tert-butyldiphenylsilyloxy)-18-(4-methoxybenzyloxy)octadec-8-yne-6,7-diol (935746-72-8) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 2: 92 percent / TsOH / CH2Cl2 / 20 °C 3: IBX / ethyl acetate / 5 h / Heating 4: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 5: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 2.1: 92 percent / p-TSA / CH2Cl2 3.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 3.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 4.1: HCl / methanol / 20 °C View Scheme

C34H54SiO4C3H2 (947304-85-0) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 2: 78 percent / aq. HCl / methanol / 20 °C View Scheme

1,9-Nonanediol (3937-56-2) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 16 steps 1: 95 percent / NaH; tetra(n-butyl)ammonium iodide / dimethylformamide / 1 h / 0 °C 2: (COCl)2; Et3N; DMSO / CH2Cl2 / -60 - 20 °C 3: 7.92 percent / benzene / 4 h / Heating 4: 96 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 5: 94 percent / TsOH / CH2Cl2 / 20 °C 6: 95 percent / DIBAL-H / CH2Cl2; toluene / 2 h / 0 - 20 °C 7: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 8: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 9: 98 percent / imidazole / CH2Cl2 / 0 °C 10: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 11: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 12: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 13: 92 percent / TsOH / CH2Cl2 / 20 °C 14: IBX / ethyl acetate / 5 h / Heating 15: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 16: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 14 steps 1.1: 95 percent / NaH / TBAI / dimethylformamide / 1 h / 0 - 20 °C 2.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - 60 °C 2.2: 91 percent / benzene / 4 h / Heating 3.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 4.1: 96 percent / p-TSA / CH2Cl2 5.1: 96 percent / DIBAL-H / CH2Cl2 / 2 h / 0 - 20 °C 6.1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 7.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 8.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 9.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 10.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 11.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 12.1: 92 percent / p-TSA / CH2Cl2 13.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 13.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 14.1: HCl / methanol / 20 °C View Scheme

(E)-1-iodohept-1-ene (60595-37-1) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions

Yield

Multi-step reaction with 7 steps 1: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 2: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 3: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 4: 92 percent / TsOH / CH2Cl2 / 20 °C 5: IBX / ethyl acetate / 5 h / Heating 6: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 7: 78 percent / aq. HCl / methanol / 20 °C View Scheme

hexanal (66-25-1) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions

Yield

Multi-step reaction with 8 steps 1: 88 percent / CrCl2 / tetrahydrofuran / 3 h / 0 °C 2: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 3: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 4: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 5: 92 percent / TsOH / CH2Cl2 / 20 °C 6: IBX / ethyl acetate / 5 h / Heating 7: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 8: 78 percent / aq. HCl / methanol / 20 °C View Scheme

9-(4-methoxybenzyloxy)nonan-1-ol (267005-80-1) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 15 steps 1: (COCl)2; Et3N; DMSO / CH2Cl2 / -60 - 20 °C 2: 7.92 percent / benzene / 4 h / Heating 3: 96 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 4: 94 percent / TsOH / CH2Cl2 / 20 °C 5: 95 percent / DIBAL-H / CH2Cl2; toluene / 2 h / 0 - 20 °C 6: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 7: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 8: 98 percent / imidazole / CH2Cl2 / 0 °C 9: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 10: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 11: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 12: 92 percent / TsOH / CH2Cl2 / 20 °C 13: IBX / ethyl acetate / 5 h / Heating 14: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 15: 78 percent / aq. HCl / methanol / 20 °C View Scheme
Multi-step reaction with 13 steps 1.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - 60 °C 1.2: 91 percent / benzene / 4 h / Heating 2.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 3.1: 96 percent / p-TSA / CH2Cl2 4.1: 96 percent / DIBAL-H / CH2Cl2 / 2 h / 0 - 20 °C 5.1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 6.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 7.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 8.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 9.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 10.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 11.1: 92 percent / p-TSA / CH2Cl2 12.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 12.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 13.1: HCl / methanol / 20 °C View Scheme

9-(4-methoxy-benzyloxy)-nonanal (531513-01-6) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions

Yield

Multi-step reaction with 14 steps 1: 7.92 percent / benzene / 4 h / Heating 2: 96 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 3: 94 percent / TsOH / CH2Cl2 / 20 °C 4: 95 percent / DIBAL-H / CH2Cl2; toluene / 2 h / 0 - 20 °C 5: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 6: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 7: 98 percent / imidazole / CH2Cl2 / 0 °C 8: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 9: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 10: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 11: 92 percent / TsOH / CH2Cl2 / 20 °C 12: IBX / ethyl acetate / 5 h / Heating 13: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 14: 78 percent / aq. HCl / methanol / 20 °C View Scheme

2,4-trans,trans-decadienal (25152-84-5) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 96 percent / BF3*OEt2 / CH2Cl2 / 0 - 22 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C 2.2: 85 percent / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: (DHQD)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO4*2H2O; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 73 h / 0 °C 4.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 5.1: 83 percent / CaCO3; Hg(ClO4)2 / tetrahydrofuran; H2O / 0.5 h / 20 °C 6.1: (S)-BINAL-H / tetrahydrofuran / 2.5 h / -78 °C 6.2: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 70 °C 7.1: 82 percent / KOH / ethanol; H2O / 46 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: 96 percent / BF3*OEt2 / CH2Cl2 / 0 - 20 °C 2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 2.2: 85 percent / 1 h / -78 °C 3.1: DHQD(PHAL)DHQD; K3[Fe(CN)6]; methanesulfonamide / K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 4.1: 89 percent / 2,6-lutidine / 0.17 h / -78 °C 5.1: 83 percent / Hg(ClO4)2; CaCO3 / tetrahydrofuran; H2O / 0.5 h / 20 °C 6.1: (S)-BINAL-H / tetrahydrofuran / 1 h / -78 °C 7.1: TBAF / tetrahydrofuran / 3 h / 70 °C 8.1: 82 percent / aq. KOH / ethanol / 46 h / 20 °C View Scheme

suberic acid monomethyl ester (3946-32-5) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 10 steps 1.1: 82 percent / (Boc)2O; 4-(dimethylamino)pyridine / 1 h / 20 °C 2.1: NaOH / tetrahydrofuran; methanol; H2O / 28 h / 20 °C 3.1: BH3*THF / tetrahydrofuran / 24 h / 0 - 20 °C 4.1: 5.53 g / imidazole; PPh3; iodine / CH2Cl2 / 0 - 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C 5.2: 85 percent / tetrahydrofuran; hexane / 1 h / -78 °C 6.1: (DHQD)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO4*2H2O; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 73 h / 0 °C 7.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 8.1: 83 percent / CaCO3; Hg(ClO4)2 / tetrahydrofuran; H2O / 0.5 h / 20 °C 9.1: (S)-BINAL-H / tetrahydrofuran / 2.5 h / -78 °C 9.2: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 70 °C 10.1: 82 percent / KOH / ethanol; H2O / 46 h / 20 °C View Scheme
Multi-step reaction with 11 steps 1.1: 82 percent / DMAP / 2-methyl-propan-2-ol / 1 h / 20 °C 2.1: aq. NaOH / tetrahydrofuran; methanol / 22 h / 20 °C 3.1: BH3*THF / tetrahydrofuran / 24 h / 0 - 20 °C 4.1: I2; PPh3; imidazole / CH2Cl2 / 1 h / 0 - 20 °C 5.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 5.2: 85 percent / 1 h / -78 °C 6.1: DHQD(PHAL)DHQD; K3[Fe(CN)6]; methanesulfonamide / K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 7.1: 89 percent / 2,6-lutidine / 0.17 h / -78 °C 8.1: 83 percent / Hg(ClO4)2; CaCO3 / tetrahydrofuran; H2O / 0.5 h / 20 °C 9.1: (S)-BINAL-H / tetrahydrofuran / 1 h / -78 °C 10.1: TBAF / tetrahydrofuran / 3 h / 70 °C 11.1: 82 percent / aq. KOH / ethanol / 46 h / 20 °C View Scheme

tert-butyl 7-(methoxycarbonyl)heptanoate (137299-08-2) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 9 steps 1.1: NaOH / tetrahydrofuran; methanol; H2O / 28 h / 20 °C 2.1: BH3*THF / tetrahydrofuran / 24 h / 0 - 20 °C 3.1: 5.53 g / imidazole; PPh3; iodine / CH2Cl2 / 0 - 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C 4.2: 85 percent / tetrahydrofuran; hexane / 1 h / -78 °C 5.1: (DHQD)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO4*2H2O; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 73 h / 0 °C 6.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 7.1: 83 percent / CaCO3; Hg(ClO4)2 / tetrahydrofuran; H2O / 0.5 h / 20 °C 8.1: (S)-BINAL-H / tetrahydrofuran / 2.5 h / -78 °C 8.2: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 70 °C 9.1: 82 percent / KOH / ethanol; H2O / 46 h / 20 °C View Scheme
Multi-step reaction with 10 steps 1.1: aq. NaOH / tetrahydrofuran; methanol / 22 h / 20 °C 2.1: BH3*THF / tetrahydrofuran / 24 h / 0 - 20 °C 3.1: I2; PPh3; imidazole / CH2Cl2 / 1 h / 0 - 20 °C 4.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 4.2: 85 percent / 1 h / -78 °C 5.1: DHQD(PHAL)DHQD; K3[Fe(CN)6]; methanesulfonamide / K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 6.1: 89 percent / 2,6-lutidine / 0.17 h / -78 °C 7.1: 83 percent / Hg(ClO4)2; CaCO3 / tetrahydrofuran; H2O / 0.5 h / 20 °C 8.1: (S)-BINAL-H / tetrahydrofuran / 1 h / -78 °C 9.1: TBAF / tetrahydrofuran / 3 h / 70 °C 10.1: 82 percent / aq. KOH / ethanol / 46 h / 20 °C View Scheme

8-(tert-butoxy)-8-oxooctanoic acid (234081-94-8) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 8 steps 1.1: BH3*THF / tetrahydrofuran / 24 h / 0 - 20 °C 2.1: 5.53 g / imidazole; PPh3; iodine / CH2Cl2 / 0 - 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C 3.2: 85 percent / tetrahydrofuran; hexane / 1 h / -78 °C 4.1: (DHQD)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO4*2H2O; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 73 h / 0 °C 5.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 6.1: 83 percent / CaCO3; Hg(ClO4)2 / tetrahydrofuran; H2O / 0.5 h / 20 °C 7.1: (S)-BINAL-H / tetrahydrofuran / 2.5 h / -78 °C 7.2: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 70 °C 8.1: 82 percent / KOH / ethanol; H2O / 46 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1.1: BH3*THF / tetrahydrofuran / 24 h / 0 - 20 °C 2.1: I2; PPh3; imidazole / CH2Cl2 / 1 h / 0 - 20 °C 3.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 3.2: 85 percent / 1 h / -78 °C 4.1: DHQD(PHAL)DHQD; K3[Fe(CN)6]; methanesulfonamide / K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 5.1: 89 percent / 2,6-lutidine / 0.17 h / -78 °C 6.1: 83 percent / Hg(ClO4)2; CaCO3 / tetrahydrofuran; H2O / 0.5 h / 20 °C 7.1: (S)-BINAL-H / tetrahydrofuran / 1 h / -78 °C 8.1: TBAF / tetrahydrofuran / 3 h / 70 °C 9.1: 82 percent / aq. KOH / ethanol / 46 h / 20 °C View Scheme

tert-butyl 8-hydroxyoctanoate (401901-41-5) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 5.53 g / imidazole; PPh3; iodine / CH2Cl2 / 0 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C 2.2: 85 percent / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: (DHQD)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO4*2H2O; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 73 h / 0 °C 4.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 5.1: 83 percent / CaCO3; Hg(ClO4)2 / tetrahydrofuran; H2O / 0.5 h / 20 °C 6.1: (S)-BINAL-H / tetrahydrofuran / 2.5 h / -78 °C 6.2: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 70 °C 7.1: 82 percent / KOH / ethanol; H2O / 46 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: I2; PPh3; imidazole / CH2Cl2 / 1 h / 0 - 20 °C 2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 2.2: 85 percent / 1 h / -78 °C 3.1: DHQD(PHAL)DHQD; K3[Fe(CN)6]; methanesulfonamide / K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 4.1: 89 percent / 2,6-lutidine / 0.17 h / -78 °C 5.1: 83 percent / Hg(ClO4)2; CaCO3 / tetrahydrofuran; H2O / 0.5 h / 20 °C 6.1: (S)-BINAL-H / tetrahydrofuran / 1 h / -78 °C 7.1: TBAF / tetrahydrofuran / 3 h / 70 °C 8.1: 82 percent / aq. KOH / ethanol / 46 h / 20 °C View Scheme

((1E,3E)-2-Nona-1,3-dienyl)-[1,3]dithiane (401901-42-6) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C 1.2: 85 percent / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: (DHQD)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO4*2H2O; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 73 h / 0 °C 3.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 4.1: 83 percent / CaCO3; Hg(ClO4)2 / tetrahydrofuran; H2O / 0.5 h / 20 °C 5.1: (S)-BINAL-H / tetrahydrofuran / 2.5 h / -78 °C 5.2: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 70 °C 6.1: 82 percent / KOH / ethanol; H2O / 46 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 1.2: 85 percent / 1 h / -78 °C 2.1: DHQD(PHAL)DHQD; K3[Fe(CN)6]; methanesulfonamide / K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 3.1: 89 percent / 2,6-lutidine / 0.17 h / -78 °C 4.1: 83 percent / Hg(ClO4)2; CaCO3 / tetrahydrofuran; H2O / 0.5 h / 20 °C 5.1: (S)-BINAL-H / tetrahydrofuran / 1 h / -78 °C 6.1: TBAF / tetrahydrofuran / 3 h / 70 °C 7.1: 82 percent / aq. KOH / ethanol / 46 h / 20 °C View Scheme

tert-butyl 8-iodooctanoate (179538-24-0) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C 1.2: 85 percent / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: (DHQD)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO4*2H2O; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 73 h / 0 °C 3.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 4.1: 83 percent / CaCO3; Hg(ClO4)2 / tetrahydrofuran; H2O / 0.5 h / 20 °C 5.1: (S)-BINAL-H / tetrahydrofuran / 2.5 h / -78 °C 5.2: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 70 °C 6.1: 82 percent / KOH / ethanol; H2O / 46 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 1.2: 85 percent / 1 h / -78 °C 2.1: DHQD(PHAL)DHQD; K3[Fe(CN)6]; methanesulfonamide / K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 3.1: 89 percent / 2,6-lutidine / 0.17 h / -78 °C 4.1: 83 percent / Hg(ClO4)2; CaCO3 / tetrahydrofuran; H2O / 0.5 h / 20 °C 5.1: (S)-BINAL-H / tetrahydrofuran / 1 h / -78 °C 6.1: TBAF / tetrahydrofuran / 3 h / 70 °C 7.1: 82 percent / aq. KOH / ethanol / 46 h / 20 °C View Scheme

8-[((1E,3E)-2-Nona-1,3-dienyl)-[1,3]dithian-2-yl]-octanoic acid tert-butyl ester (401901-43-7) → (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: (DHQD)2PHAL; K3[Fe(CN)6]; K2CO3 / K2OsO4*2H2O; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 73 h / 0 °C 2.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 3.1: 83 percent / CaCO3; Hg(ClO4)2 / tetrahydrofuran; H2O / 0.5 h / 20 °C 4.1: (S)-BINAL-H / tetrahydrofuran / 2.5 h / -78 °C 4.2: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 70 °C 5.1: 82 percent / KOH / ethanol; H2O / 46 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: DHQD(PHAL)DHQD; K3[Fe(CN)6]; methanesulfonamide / K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 1 h / 0 °C 2: 89 percent / 2,6-lutidine / 0.17 h / -78 °C 3: 83 percent / Hg(ClO4)2; CaCO3 / tetrahydrofuran; H2O / 0.5 h / 20 °C 4: (S)-BINAL-H / tetrahydrofuran / 1 h / -78 °C 5: TBAF / tetrahydrofuran / 3 h / 70 °C 6: 82 percent / aq. KOH / ethanol / 46 h / 20 °C View Scheme

(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7) + diazomethyl-trimethyl-silane (18107-18-1) → methyl (9S,10E,12S,13S)-9,12,13-trihydroxy-10-octadecenoate (93380-89-3)

Conditions	Yield
In methanol; hexane; benzene at 20℃; for 2.5h;	100%

diazomethane (186581-53-3, 908094-01-9) + (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7) → methyl (9S,10E,12S,13S)-9,12,13-trihydroxy-10-octadecenoate (93380-89-3)

Conditions	Yield
In diethyl ether

(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7) → (S,E)-methyl 9-hydroxy-11-((4R,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)-undec-10-enoate

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / benzene; methanol; hexane / 2.5 h / 20 °C 2: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 48 h / 60 °C View Scheme

(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid (97134-11-7) → 9-(4-bromobenzoyloxy)-12,13-O-isopropylidene-9,12,13-trihydroxyoctadec-10-enoic acid methyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / benzene; methanol; hexane / 2.5 h / 20 °C 2: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 48 h / 60 °C 3: pyridine; 4-(dimethylamino)pyridine / 10 h / 20 °C View Scheme

Upstream product

• 401901-48-2 (9S,12S,13S)-(E)-9,12,13-trihydroxy-10-octadecenoic acid tert-butyl ester 
• 935746-75-1 (S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid 
• 935746-69-3 (S)-11-(4-methoxybenzyloxy)undec-1-yn-3-ol 
• 935746-64-8 (E)-ethyl 11-(4-methoxybenzyloxy)undec-2-enoate 
• 935746-67-1 ((4S,5S)-5-(8-(4-methoxybenzyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 
• 935746-68-2 (4S,5R)-4-(8-(4-methoxybenzyloxy)octyl)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolane 
• 935746-66-0 (4R,5S)-ethyl 5-(8-(4-methoxybenzyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 935746-65-9 (2R,3S)-ethyl 11-(4-methoxybenzyloxy)-2,3-dihydroxyundecanoate 
• 935746-70-6 ((S)-11-(4-methoxybenzyloxy)undec-1-yn-3-yloxy)(tert-butyl)diphenylsilane 
• 935746-73-9 (9S,12S,13S,E)-9-(tert-butyldiphenylsilyloxy)-octadec-10-ene-1,12,13-triol 
• 935746-74-0 (S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-en-1-ol 
• 935746-71-7 ((S,E)-1-(4-methoxybenzyloxy)octadec-12-en-10-yn-9-yloxy)(tert-butyl)diphenylsilane 
• 935746-72-8 (6S,7S,10S)-10-(tert-butyldiphenylsilyloxy)-18-(4-methoxybenzyloxy)octadec-8-yne-6,7-diol 
• 947304-85-0 C₃₄H₅₄SiO₄C₃H₂ 

Downstream Products

• 132624-98-7 Benzoic acid (S)-1-[(E)-2-((4S,5S)-2,2-dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-vinyl]-8-methoxycarbonyl-octyl ester 

Relevant articles and documents

Molecular characterization of NbEH1 and NbEH2, two epoxide hydrolases from Nicotiana benthamiana

Plant epoxide hydrolases (EH) form two major clades, named EH1 and EH2. To gain a better understanding of the biochemical roles of the two classes, NbEH1.1 and NbEH2.1 were isolated from Nicotiana benthamiana and StEH from potato and heterologously expressed in Escherichia coli. The purified recombinant proteins were assayed with a variety of substrates. NbEH1.1 only accepted some aromatic epoxides, and displayed the highest enzyme activity towards phenyl glycidyl ether. In contrast, NbEH2.1 displayed a broad substrate range and similar substrate specificity as StEH. The latter enzymes showed activity towards all fatty acid epoxides examined. The activity (Vmax) of NbEH1.1 towards phenyl glycidyl ether was 10 times higher than that of NbEH2.1. On the contrary, NbEH2.1 converted cis-9,10-epoxystearic acid with Vmax of 3.83 μmol min mg-1 but NbEH1.1 could not hydrolyze cis-9,10- epoxystearic acid. Expression analysis revealed that NbEH1.1 is induced by infection with tobacco mosaic virus (TMV) and wounding, whereas NbEH2.1 is present at a relatively constant level, not influenced by treatment with TMV and wounding. NbEH1.1 transcripts were present predominantly in roots, whereas NbEH2.1 mRNAs were detected primarily in leaves and stems. Overall, these two types of tobacco EH enzymes are distinguished not only by their gene expression, but also by different substrate specificities. EH1 seems not to participate in cutin biosynthesis and it may play a role in generating signals for activation of certain defence and stress responses in tobacco. However, members of the EH2 group hydrate fatty acid epoxides and may be involved in cutin monomer production in plants.

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