(6R)-8-(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-xy}-5-oxatricyclo[8.4.0.0]tetradeca-1⁽¹⁴⁾,2,7,10,12-pentaen-4-one

Base Information

• Chemical Name: (6R)-8-(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-xy}-5-oxatricyclo[8.4.0.0]tetradeca-1⁽¹⁴⁾,2,7,10,12-pentaen-4-one
• CAS No.: 1432518-79-0
• Molecular Formula: C₂₉H₃₁FO₅S
• Molecular Weight: 510.627

Synonyms:(6R)-8-(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-xy}-5-oxatricyclo[8.4.0.0]tetradeca-1⁽¹⁴⁾,2,7,10,12-pentaen-4-one

Chemical Property of (6R)-8-(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-xy}-5-oxatricyclo[8.4.0.0]tetradeca-1⁽¹⁴⁾,2,7,10,12-pentaen-4-one

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Technology Process of (6R)-8-(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-xy}-5-oxatricyclo[8.4.0.0]tetradeca-1⁽¹⁴⁾,2,7,10,12-pentaen-4-one

There total 10 articles about (6R)-8-(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-xy}-5-oxatricyclo[8.4.0.0]tetradeca-1⁽¹⁴⁾,2,7,10,12-pentaen-4-one 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: 45.0%

(6R,7R)-8,8-bis(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-5-oxatricyclo[8.4.0.0]tetradeca-1(14),2,10,12-tetraen-4-one (1432519-32-8) → (6R)-8-(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-xy}-5-oxatricyclo[8.4.0.0]tetradeca-1(14),2,7,10,12-pentaen-4-one (1432518-79-0)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at 0 ℃; for 2.5h; Cooling with ice;

DOI:10.1039/c3ob40115d

Reference yield:

C23H23FO2S2 → (6R)-8-(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-xy}-5-oxatricyclo[8.4.0.0]tetradeca-1(14),2,7,10,12-pentaen-4-one (1432518-79-0)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogenchloride / hexane; tetrahydrofuran; water / 3 h / Cooling with ice

2: n-butyllithium; diphenyl diselenide / hexane; tetrahydrofuran / 8 h / -60 - -20 °C

3: dmap; pyridine / dichloromethane / 3 h / 0 °C / Cooling with ice

4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 7 h / 0 °C / Cooling with ice

5: caesium carbonate / tetrahydrofuran / 1.33 h / 0 - 20 °C / Cooling with ice

6: sodium amalgam; disodium hydrogenphosphate / methanol / 2.5 h / 0 °C / Cooling with ice

With pyridine; hydrogenchloride; dmap; disodium hydrogenphosphate; n-butyllithium; diphenyl diselenide; sodium amalgam; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water;

DOI:10.1039/c3ob40115d

Reference yield:

3-fluoro-6-methylbenzonitrile (77532-79-7) → (6R)-8-(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-xy}-5-oxatricyclo[8.4.0.0]tetradeca-1(14),2,7,10,12-pentaen-4-one (1432518-79-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane

2.1: diisobutylaluminium hydride; hydrogen bromide / dichloromethane / Cooling with ice

3.1: toluene-4-sulfonic acid / methanol / 1 h / 50 °C

4.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 - 0 °C / Cooling with ice

4.2: 0.67 h / -78 - 0 °C / Cooling with ice

5.1: hydrogenchloride / hexane; tetrahydrofuran; water / 3 h / Cooling with ice

6.1: n-butyllithium; diphenyl diselenide / hexane; tetrahydrofuran / 8 h / -60 - -20 °C

7.1: dmap; pyridine / dichloromethane / 3 h / 0 °C / Cooling with ice

8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 7 h / 0 °C / Cooling with ice

9.1: caesium carbonate / tetrahydrofuran / 1.33 h / 0 - 20 °C / Cooling with ice

10.1: sodium amalgam; disodium hydrogenphosphate / methanol / 2.5 h / 0 °C / Cooling with ice

With pyridine; hydrogenchloride; dmap; disodium hydrogenphosphate; N-Bromosuccinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); diphenyl diselenide; sodium amalgam; hydrogen bromide; diisobutylaluminium hydride; caesium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water;

DOI:10.1039/c3ob40115d

upstream raw materials:

3-fluoro-6-methylbenzonitrile

2-(bromomethyl)-5-fluorobenzonitrile

2-(bromomethyl)-5-fluorobenzaldehyde

1-(bromomethyl)-2-(dimethoxymethyl)-4-fluorobenzene

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