9-OXO-11ALPHA,16R-DIHYDROXY-17-CYCLOBUTYL-5Z,13E-DIEN-1-OIC ACID

Base Information

• Chemical Name: 9-OXO-11ALPHA,16R-DIHYDROXY-17-CYCLOBUTYL-5Z,13E-DIEN-1-OIC ACID
• CAS No.: 212310-16-2
• Molecular Formula: C₂₃H₃₆O₅
• Molecular Weight: 392.536
• Mol file: 212310-16-2.mol

Synonyms:5-Heptenoicacid,7-[(1R,2R,3R)-3-hydroxy-2-[(1E,4R)-4-hydroxy-4-(1-propylcyclobutyl)-1-butenyl]-5-oxocyclopentyl]-,(5Z)- (9CI)

Chemical Property of 9-OXO-11ALPHA,16R-DIHYDROXY-17-CYCLOBUTYL-5Z,13E-DIEN-1-OIC ACID

Chemical Property:

• PSA: 94.83000
• LogP: 4.03130

Purity/Quality:

99% ^*data from raw suppliers

CAY10408 ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 9-OXO-11ALPHA,16R-DIHYDROXY-17-CYCLOBUTYL-5Z,13E-DIEN-1-OIC ACID

There total 19 articles about 9-OXO-11ALPHA,16R-DIHYDROXY-17-CYCLOBUTYL-5Z,13E-DIEN-1-OIC 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: 86.0%

(Z)-7-{(1R,2R,3R)-3-Hydroxy-2-[(E)-(S)-4-hydroxy-4-(1-propyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester (212309-91-6) → CAY10399 (212310-16-2)

Guidance literature:

With porcine liver esterase; ammonium sulfate; In phosphate buffer; ethanol; at 20 ℃; for 6h; pH=7.4;

DOI:10.1016/S0968-0896(01)00369-8

Reference yield:

(Z)-7-{(1R,2R,3R)-3-Hydroxy-2-[(E)-(R)-4-hydroxy-4-(1-propyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester (212309-90-5) → CAY10408 (212310-16-2)

Guidance literature:

With porcine liver esterase; ammonium sulfate; In phosphate buffer; ethanol; at 20 ℃; for 6h; pH=7.4;

DOI:10.1016/S0968-0896(01)00369-8

Reference yield:

Cyclobutanecarboxylic acid (3721-95-7) → CAY10408 (212310-16-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 12 h / 20 °C

2.1: 100 percent / LiAlH₄ / diethyl ether / 3.5 h / 20 °C

3.1: 59 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4.1: Mg; mercuric chloride / diethyl ether / 0.17 h / 0 °C

4.2: 85 percent / diethyl ether / 1 h / 20 °C

5.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 - 20 °C

6.1: Cp₂ZrClH / tetrahydrofuran / 0.5 h / 20 °C

6.2: 86 percent / I₂ / tetrahydrofuran / 0.17 h / 20 °C

7.1: 66 percent / t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / 1 h / -78 - 0 °C

8.1: 48 percent / aq. HF / acetonitrile / 1.5 h / 20 °C

9.1: porcine liver esterase; aq. ammonium sulfate / ethanol; aq. phosphate buffer / 6 h / 20 °C / pH 7.4

With 2,6-dimethylpyridine; porcine liver esterase; ammonium sulfate; lithium aluminium tetrahydride; Schwartz's reagent; oxalyl dichloride; hydrogen fluoride; tert.-butyl lithium; magnesium; dimethyl sulfoxide; thien-2-yl(cyano)copper lithium; triethylamine; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; phosphate buffer; diethyl ether; ethanol; dichloromethane; acetonitrile; pentane; 3.1: Swern oxidation;

DOI:10.1016/S0968-0896(01)00369-8

upstream raw materials:

(Z)-7-{(1R,2R,3R)-3-Hydroxy-2-[(E)-(R)-4-hydroxy-4-(1-propyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

(Z)-7-{(1R,2R,3R)-3-Hydroxy-2-[(E)-(S)-4-hydroxy-4-(1-propyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

Cyclobutanecarboxylic acid

2,2-trimethylenepentanoic acid