(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

Base Information

• Chemical Name: (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
• CAS No.: 433220-29-2
• Molecular Formula: C₄₀H₇₂O₅Si₂
• Molecular Weight: 689.18

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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:

Methyl (Z)-7-<(3R)-3-<(tert-Butyldimethylsilyl)oxy>-5-oxo-1-cyclopentenyl>-5-heptenoate (82542-42-5,132619-70-6) + (E)-1-iodo-4-(tert-butyldimethylsiloxy)-6-cyclohexyl-5,5-trimethylene-1-hexene (433220-14-5) → (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 (433220-29-2)

Guidance literature:

With tert.-butyl lithium; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; pentane; at -78 - 0 ℃; for 1h;

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

Reference yield:

Cyclobutanecarboxylic acid (3721-95-7) → (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 (433220-29-2)

Guidance literature:

Multi-step reaction with 7 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

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 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; pentane; 3.1: Swern oxidation;

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

Reference yield:

cyclohexylmethyl iodide (5469-33-0) → (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 (433220-29-2)

Guidance literature:

Multi-step reaction with 7 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

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 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; pentane; 3.1: Swern oxidation;

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

upstream raw materials:

Methyl (Z)-7-<(3R)-3-<(tert-Butyldimethylsilyl)oxy>-5-oxo-1-cyclopentenyl>-5-heptenoate

(E)-1-iodo-4-(tert-butyldimethylsiloxy)-6-cyclohexyl-5,5-trimethylene-1-hexene

Cyclobutanecarboxylic acid

cyclohexylmethyl iodide

Downstream raw materials:

(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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