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

Base Information

Chemical Name:(Z)-7-{(1R,2R,3R)-2-[(E)-(R)-4-(1-Cyclohexylmethyl-cyclobutyl)-4-hydroxy-but-1-enyl]-3-hydroxy-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester
CAS No.:212310-12-8
Molecular Formula:C₂₈H₄₄O₅
Molecular Weight:460.654
Hs Code.:

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

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

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

There total 9 articles about (Z)-7-{(1R,2R,3R)-2-[(E)-(R)-4-(1-Cyclohexylmethyl-cyclobutyl)-4-hydroxy-but-1-enyl]-3-hydroxy-5-oxo-cyclopentyl}-hept-5-enoic acid methyl 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:

: 433220-29-2
(Z)-7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-cyclohexylmethyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

: 212310-12-8
(Z)-7-{(1R,2R,3R)-2-[(E)-(R)-4-(1-Cyclohexylmethyl-cyclobutyl)-4-hydroxy-but-1-enyl]-3-hydroxy-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

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

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 20 ℃; for 1.5h;
DOI:10.1016/S0968-0896(01)00369-8

Reference yield:

: 3721-95-7
Cyclobutanecarboxylic acid

: 212310-12-8
(Z)-7-{(1R,2R,3R)-2-[(E)-(R)-4-(1-Cyclohexylmethyl-cyclobutyl)-4-hydroxy-but-1-enyl]-3-hydroxy-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

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

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

3.1: (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: diethyl ether / 1 h / 20 °C

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

6.1: n-Bu₃SnH; AIBN / 2 h / 80 °C

6.2: I₂ / diethyl ether / 0.17 h / 0 °C

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

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

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tert.-butyl lithium; tri-n-butyl-tin hydride; magnesium; dimethyl sulfoxide; thien-2-yl(cyano)copper lithium; triethylamine; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; pentane; 3.1: Swern oxidation;
DOI:10.1016/S0968-0896(01)00369-8

Reference yield:

: 5469-33-0
cyclohexylmethyl iodide

: 212310-12-8
(Z)-7-{(1R,2R,3R)-2-[(E)-(R)-4-(1-Cyclohexylmethyl-cyclobutyl)-4-hydroxy-but-1-enyl]-3-hydroxy-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

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

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

3.1: (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: diethyl ether / 1 h / 20 °C

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

6.1: n-Bu₃SnH; AIBN / 2 h / 80 °C

6.2: I₂ / diethyl ether / 0.17 h / 0 °C

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

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

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tert.-butyl lithium; tri-n-butyl-tin hydride; magnesium; dimethyl sulfoxide; thien-2-yl(cyano)copper lithium; triethylamine; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; pentane; 3.1: Swern oxidation;
DOI:10.1016/S0968-0896(01)00369-8