6-[(1R,2R,3S,5S)-2-((E)-4-Carboxy-but-2-enyl)-3,5-dihydroxy-cyclopentyl]-4-oxo-hexanoic acid

Base Information

• Chemical Name: 6-[(1R,2R,3S,5S)-2-((E)-4-Carboxy-but-2-enyl)-3,5-dihydroxy-cyclopentyl]-4-oxo-hexanoic acid
• CAS No.: 34069-64-2
• Molecular Formula: C₁₆H₂₄O₇
• Molecular Weight: 328.362
• Mol file: 34069-64-2.mol

Synonyms:

Chemical Property of 6-[(1R,2R,3S,5S)-2-((E)-4-Carboxy-but-2-enyl)-3,5-dihydroxy-cyclopentyl]-4-oxo-hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[(1R,2R,3S,5S)-2-((E)-4-Carboxy-but-2-enyl)-3,5-dihydroxy-cyclopentyl]-4-oxo-hexanoic acid

There total 16 articles about 6-[(1R,2R,3S,5S)-2-((E)-4-Carboxy-but-2-enyl)-3,5-dihydroxy-cyclopentyl]-4-oxo-hexanoic acid 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:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → 6-[(1R,2R,3S,5S)-2-((E)-4-Carboxy-but-2-enyl)-3,5-dihydroxy-cyclopentyl]-4-oxo-hexanoic acid (34069-64-2,99437-87-3,133161-96-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) dicyclohexylcarbodi-imide; 2.) dichloroacetic acid; 3.) oxalic acid / 1.) benzene, DMSO, 5 min; 2.) 20 min, 3.) methanol, 10 min

2: tetrahydrofuran / 3 h / Ambient temperature

3: 90 percent / H₂ / palladium-carbon / ethyl acetate / 4 h / Ambient temperature

4: 82 percent / zinc triflate / CH₂Cl₂ / 2 h / Ambient temperature

5: 88 percent / t-BuOK / methanol; methyl acetate / 2 h / Ambient temperature

6: 70 percent / toluene-p-sulphonic acid / CH₂Cl₂ / 1 h / Ambient temperature

7: 92 percent / DIBAL / tetrahydrofuran / 0.5 h / -78 °C

8: 1.) lithium bis(trimethylsilyl)amide / 1.) THF-HMPA, 0 deg C, 30 min; 2.) -40 to 0 deg C, THF, 30 min then 0 deg C, 2 h

9: 1.) NaHSO₄; 2.) LiOH / 1.) water, DME, pH 3, 0 deg C, 20 min; 2.) water, RT, 1 h

10: tetramethylammonium hydroxide / dimethylformamide / 0.33 h / 0 °C

11: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

12: cation exchange resin AG₅₀-X₈ / methanol / 6 h / 23 °C

13: triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

14: 18-crown-6-ether / toluene / 8 h / 115 °C / Heating

15: ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

16: LiOH / 1,2-dimethoxy-ethane; H₂O / 1 h / Ambient temperature

With pyridine; dichloro-acetic acid; lithium hydroxide; sodium hydrogen sulfate; ammonium cerium(IV) nitrate; 18-crown-6 ether; cation exchange resin AG₅₀-X₈; potassium tert-butylate; tetramethyl ammoniumhydroxide; hydrogen; oxalic acid; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; acetic acid methyl ester; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/P19880002821

Reference yield:

3-{2-[2-((3aR,4R,5R,6aS)-5-Hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-4-yl)-ethyl]-[1,3]dithiolan-2-yl}-propionic acid methyl ester (118908-19-3) → 6-[(1R,2R,3S,5S)-2-((E)-4-Carboxy-but-2-enyl)-3,5-dihydroxy-cyclopentyl]-4-oxo-hexanoic acid (34069-64-2,99437-87-3,133161-96-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 70 percent / toluene-p-sulphonic acid / CH₂Cl₂ / 1 h / Ambient temperature

2: 92 percent / DIBAL / tetrahydrofuran / 0.5 h / -78 °C

3: 1.) lithium bis(trimethylsilyl)amide / 1.) THF-HMPA, 0 deg C, 30 min; 2.) -40 to 0 deg C, THF, 30 min then 0 deg C, 2 h

4: 1.) NaHSO₄; 2.) LiOH / 1.) water, DME, pH 3, 0 deg C, 20 min; 2.) water, RT, 1 h

5: tetramethylammonium hydroxide / dimethylformamide / 0.33 h / 0 °C

6: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

7: cation exchange resin AG₅₀-X₈ / methanol / 6 h / 23 °C

8: triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

9: 18-crown-6-ether / toluene / 8 h / 115 °C / Heating

10: ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

11: LiOH / 1,2-dimethoxy-ethane; H₂O / 1 h / Ambient temperature

With pyridine; lithium hydroxide; sodium hydrogen sulfate; ammonium cerium(IV) nitrate; 18-crown-6 ether; cation exchange resin AG₅₀-X₈; tetramethyl ammoniumhydroxide; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/P19880002821

Reference yield:

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-(5-methoxycarbonyl-3-oxo-pentyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (118908-17-1) → 6-[(1R,2R,3S,5S)-2-((E)-4-Carboxy-but-2-enyl)-3,5-dihydroxy-cyclopentyl]-4-oxo-hexanoic acid (34069-64-2,99437-87-3,133161-96-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 82 percent / zinc triflate / CH₂Cl₂ / 2 h / Ambient temperature

2: 88 percent / t-BuOK / methanol; methyl acetate / 2 h / Ambient temperature

3: 70 percent / toluene-p-sulphonic acid / CH₂Cl₂ / 1 h / Ambient temperature

4: 92 percent / DIBAL / tetrahydrofuran / 0.5 h / -78 °C

5: 1.) lithium bis(trimethylsilyl)amide / 1.) THF-HMPA, 0 deg C, 30 min; 2.) -40 to 0 deg C, THF, 30 min then 0 deg C, 2 h

6: 1.) NaHSO₄; 2.) LiOH / 1.) water, DME, pH 3, 0 deg C, 20 min; 2.) water, RT, 1 h

7: tetramethylammonium hydroxide / dimethylformamide / 0.33 h / 0 °C

8: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

9: cation exchange resin AG₅₀-X₈ / methanol / 6 h / 23 °C

10: triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

11: 18-crown-6-ether / toluene / 8 h / 115 °C / Heating

12: ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

13: LiOH / 1,2-dimethoxy-ethane; H₂O / 1 h / Ambient temperature

With pyridine; lithium hydroxide; sodium hydrogen sulfate; ammonium cerium(IV) nitrate; 18-crown-6 ether; cation exchange resin AG₅₀-X₈; potassium tert-butylate; tetramethyl ammoniumhydroxide; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; acetic acid methyl ester; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/P19880002821

upstream raw materials:

6-[(1R,2R,3S,5S)-3,5-Diacetoxy-2-((E)-4-methoxycarbonyl-but-2-enyl)-cyclopentyl]-4-oxo-hexanoic acid methyl ester

(-)-Corey lactone 5-(4-phenylbenzoate)

3-{2-[2-((3aR,4R,5R,6aS)-5-Hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-4-yl)-ethyl]-[1,3]dithiolan-2-yl}-propionic acid methyl ester

3-(2-{2-[(3aR,4R,5R,6aS)-2-Hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-ethyl}-[1,3]dithiolan-2-yl)-propionic acid methyl ester