(Z)-7-{(1R,2R,3R)-2-[(1E,5E)-3-(benzyloxy)-4,4-difluoro-oct-1,5-dien-1-yl]-3-[(tert-butyldimethylsilanyl)oxy]-5-oxo-cyclopentyl}hept-5-enoic acid isopropyl ester

Base Information

Chemical Name:(Z)-7-{(1R,2R,3R)-2-[(1E,5E)-3-(benzyloxy)-4,4-difluoro-oct-1,5-dien-1-yl]-3-[(tert-butyldimethylsilanyl)oxy]-5-oxo-cyclopentyl}hept-5-enoic acid isopropyl ester
CAS No.:1372609-13-6
Molecular Formula:C₃₆H₅₄F₂O₅Si
Molecular Weight:632.904
Hs Code.:

(Z)-7-{(1R,2R,3R)-2-[(1E,5E)-3-(benzyloxy)-4,4-difluoro-oct-1,5-dien-1-yl]-3-[(tert-butyldimethylsilanyl)oxy]-5-oxo-cyclopentyl}hept-5-enoic acid isopropyl ester

Synonyms:(Z)-7-{(1R,2R,3R)-2-[(1E,5E)-3-(benzyloxy)-4,4-difluoro-oct-1,5-dien-1-yl]-3-[(tert-butyldimethylsilanyl)oxy]-5-oxo-cyclopentyl}hept-5-enoic acid isopropyl ester

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Chemical Property of (Z)-7-{(1R,2R,3R)-2-[(1E,5E)-3-(benzyloxy)-4,4-difluoro-oct-1,5-dien-1-yl]-3-[(tert-butyldimethylsilanyl)oxy]-5-oxo-cyclopentyl}hept-5-enoic acid isopropyl ester

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Technology Process of (Z)-7-{(1R,2R,3R)-2-[(1E,5E)-3-(benzyloxy)-4,4-difluoro-oct-1,5-dien-1-yl]-3-[(tert-butyldimethylsilanyl)oxy]-5-oxo-cyclopentyl}hept-5-enoic acid isopropyl ester

There total 12 articles about (Z)-7-{(1R,2R,3R)-2-[(1E,5E)-3-(benzyloxy)-4,4-difluoro-oct-1,5-dien-1-yl]-3-[(tert-butyldimethylsilanyl)oxy]-5-oxo-cyclopentyl}hept-5-enoic acid isopropyl 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: 28.0%

: 1372609-13-6
(Z)-7-{(1R,2R,3R)-2-[(1E,5E)-3-(benzyloxy)-4,4-difluoro-oct-1,5-dien-1-yl]-3-[(tert-butyldimethylsilanyl)oxy]-5-oxo-cyclopentyl}hept-5-enoic acid isopropyl ester

Guidance literature:: With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide; In methanol; water; at 30 ℃; for 6h; Microwave irradiation;

Reference yield:

: 474944-36-0
(Z)-7-[(3R)-3-(tert-butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid isopropyl ester

: 1372609-21-6
((1E,5E)-3-(benzyloxy)-4,4-difluoroocta-1,5-dienyl)tributylstannane

: 1372609-13-6
(Z)-7-{(1R,2R,3R)-2-[(1E,5E)-3-(benzyloxy)-4,4-difluoro-oct-1,5-dien-1-yl]-3-[(tert-butyldimethylsilanyl)oxy]-5-oxo-cyclopentyl}hept-5-enoic acid isopropyl ester

Guidance literature:: ((1E,5E)-3-(benzyloxy)-4,4-difluoroocta-1,5-dienyl)tributylstannane; With methyllithium; In tetrahydrofuran; formaldehyde diethyl acetal; at -70 - -60 ℃; for 0.5h; Inert atmosphere;

With methyllithium; copper(l) cyanide; In tetrahydrofuran; formaldehyde diethyl acetal; at -50 - -40 ℃; for 0.5h; Inert atmosphere;

(Z)-7-[(3R)-3-(tert-butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid isopropyl ester; In tetrahydrofuran; formaldehyde diethyl acetal; at -60 - -50 ℃; Product distribution / selectivity;

Reference yield:

: 156544-72-8
2,2-difluoro-3-hydroxyhexanoic acid ethyl ester

: 1372609-13-6
(Z)-7-{(1R,2R,3R)-2-[(1E,5E)-3-(benzyloxy)-4,4-difluoro-oct-1,5-dien-1-yl]-3-[(tert-butyldimethylsilanyl)oxy]-5-oxo-cyclopentyl}hept-5-enoic acid isopropyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine / dichloromethane / 0 - 15 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tert-butyl methyl ether / Reflux

3.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere

3.2: -78 - -60 °C / Inert atmosphere

3.3: -78 - 10 °C

4.1: sodium tetrahydroborate; methanol / -5 - 0 °C

4.2: -5 - 0 °C / pH 5 - 6

5.1: potassium tert-butylate / tetrahydrofuran / 1 h / 60 - 70 °C

6.1: 2,2'-azobis(isobutyronitrile) / toluene / 80 - 85 °C

7.1: methyllithium / formaldehyde diethyl acetal; tetrahydrofuran / 0.5 h / -70 - -60 °C / Inert atmosphere

7.2: 0.5 h / -50 - -40 °C / Inert atmosphere

7.3: -60 - -50 °C

With pyridine; methanol; sodium tetrahydroborate; n-butyllithium; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; methyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; formaldehyde diethyl acetal; dichloromethane; tert-butyl methyl ether; toluene;