8-[(1R,2S,3S,5R)-2-(2-Carboxy-ethyl)-3,5-dihydroxy-cyclopentyl]-6-oxo-octanoic acid

Base Information

• Chemical Name: 8-[(1R,2S,3S,5R)-2-(2-Carboxy-ethyl)-3,5-dihydroxy-cyclopentyl]-6-oxo-octanoic acid
• CAS No.: 925433-33-6
• Molecular Formula: C₁₆H₂₆O₇
• Molecular Weight: 330.378
• Mol file: 925433-33-6.mol

Synonyms:

Chemical Property of 8-[(1R,2S,3S,5R)-2-(2-Carboxy-ethyl)-3,5-dihydroxy-cyclopentyl]-6-oxo-octanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-[(1R,2S,3S,5R)-2-(2-Carboxy-ethyl)-3,5-dihydroxy-cyclopentyl]-6-oxo-octanoic acid

There total 12 articles about 8-[(1R,2S,3S,5R)-2-(2-Carboxy-ethyl)-3,5-dihydroxy-cyclopentyl]-6-oxo-octanoic 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:

(1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane (552833-10-0) → 8-[(1R,2S,3S,5R)-2-(2-Carboxy-ethyl)-3,5-dihydroxy-cyclopentyl]-6-oxo-octanoic acid (925433-33-6)

Guidance literature:

With sodium hydroxide; water; at 40 ℃;

DOI:10.1016/S0040-4039(01)00754-7

Reference yield:

(1R,2R,3S,4S)-1,4-di(benzoyloxy)-2-formyl-3-(2-methoxycarbonylethyl)cyclopentane (358395-65-0) → 8-[(1R,2S,3S,5R)-2-(2-Carboxy-ethyl)-3,5-dihydroxy-cyclopentyl]-6-oxo-octanoic acid (925433-33-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 258 mg / NaH / tetrahydrofuran / 0.17 h / 20 °C

2: 100 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / atmospheric pressure

3: 1N NaOH / methanol; tetrahydrofuran / 2 h / 40 °C

With sodium hydroxide; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol;

DOI:10.1016/S0040-4020(03)00258-8

Reference yield:

tert-Butyl-[(R)-2-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-iodo-ethoxy]-diphenyl-silane → 8-[(1R,2S,3S,5R)-2-(2-Carboxy-ethyl)-3,5-dihydroxy-cyclopentyl]-6-oxo-octanoic acid (925433-33-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 71 percent / ZnCl₂ / 0.5 h / -20 °C

2: 88 percent / pyridine / 20 °C

3: 100 percent / HgO; HgCl₂ / acetone; H₂O / Heating

4: 74 percent / KHMDS / tetrahydrofuran / 1 h / -80 - 20 °C

5: Jones reagent / acetone / 2 h / -10 - 20 °C

6: 401 mg / diethyl ether

7: 72 percent / Bu₃SnH; BEt₃; O₂ / p-xylene / 0.67 h / 20 °C

8: 68 percent / HCl / diethyl ether; methanol / 20 h / 20 °C

9: Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.5 h / 20 °C

10: 258 mg / NaH / tetrahydrofuran / 0.17 h / 20 °C

11: 100 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / atmospheric pressure

12: 1N NaOH / methanol; tetrahydrofuran / 2 h / 40 °C

With hydrogenchloride; sodium hydroxide; jones reagent; triethyl borane; hydrogen; oxygen; tri-n-butyl-tin hydride; potassium hexamethylsilazane; sodium hydride; Dess-Martin periodane; mercury dichloride; mercury(II) oxide; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; para-xylene; water; acetone; 9: Dess-Martin oxidation;

DOI:10.1016/S0040-4020(03)00258-8

upstream raw materials:

(1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane

(1R,2R,3S,4S)-1,4-di(benzoyloxy)-2-formyl-3-(2-methoxycarbonylethyl)cyclopentane

(1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane

(2S,4R,5R)-6-(tert-butyldiphenylsilyloxy)-1,1-diethylthio-5-iodohexane-2,4-diol