[(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester

Base Information

• Chemical Name: [(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester
• CAS No.: 944340-53-8
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 944340-53-8.mol

Synonyms:[(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester

Chemical Property of [(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester

There total 11 articles about [(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester (869476-96-0) → [(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester (944340-53-8)

Guidance literature:

With hydrogenchloride; In water; acetonitrile; at 20 ℃; for 1h;

Reference yield:

(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one (115509-13-2) → [(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester (944340-53-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C

2: 57 percent / LHMDS; HMPA; Me₂Zn / tetrahydrofuran; toluene / -78 - -45 °C

3: KHMDS; CeCl₃ / tetrahydrofuran / -45 °C

4: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

5: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran

6: aq. HCl / acetonitrile; H₂O / 0.75 h / 23 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; cerium(III) chloride; hydrogen; dimethyl zinc(II); potassium hexamethylsilazane; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; toluene; acetonitrile; 3: Wittig reaction / 5: Mitsunobu reaction;

DOI:10.1021/jo071146k

Reference yield:

(4R,5R)-1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)prop-2-en-1-ol (683276-43-9) → [(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester (944340-53-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Grubbs catalyst / CH₂Cl₂ / 4 h / 23 °C

1.2: 87 percent / pyridinium chlorochromate / CH₂Cl₂ / 12 h / 23 °C

2.1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C

3.1: 57 percent / LHMDS; HMPA; Me₂Zn / tetrahydrofuran; toluene / -78 - -45 °C

4.1: KHMDS; CeCl₃ / tetrahydrofuran / -45 °C

5.1: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

6.1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran

7.1: aq. HCl / acetonitrile; H₂O / 0.75 h / 23 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; cerium(III) chloride; hydrogen; dimethyl zinc(II); potassium hexamethylsilazane; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 4.1: Wittig reaction / 6.1: Mitsunobu reaction;

DOI:10.1021/jo071146k

upstream raw materials:

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester

((3aR,5S,6aR)-2,2-dimethyl-4-oxotetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl)acetic acid methyl ester

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid methyl ester

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid

Downstream raw materials:

(3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester

Oleocanthal