(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

Base Information

• Chemical Name: (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
• CAS No.: 1432519-32-8
• Molecular Formula: C₃₅H₃₇FO₇S₂
• Molecular Weight: 652.805

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 9 articles about (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 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: 99.0%

(S)-{2-[2,2-bis(benzenesulfonyl)ethyl]-5-fluorophenyl}[(5R)-5-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-2-oxo-2,5-dihydrofuran-3-yl]methyl acetate (1432519-16-8) → (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)

Guidance literature:

With caesium carbonate; In tetrahydrofuran; at 0 - 20 ℃; for 1.33333h; Cooling with ice;

DOI:10.1039/c3ob40115d

Reference yield:

C23H23FO2S2 → (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)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1039/c3ob40115d

Reference yield:

3-fluoro-6-methylbenzonitrile (77532-79-7) → (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)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; hydrogenchloride; dmap; N-Bromosuccinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); diphenyl diselenide; 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

Downstream raw materials:

(2Z)-2-({2-[2-(benzenesulfonyl)ethyl]-5-fluorophenyl}methyl)but-2-ene-1,4-diol

(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

(3S,6R,7R)-8,8-bis(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5methyl-2-(propan-2-yl)cyclohexyl]oxy}-5-oxatricyclo[8.4.0.03,7]tetradeca-1⁽¹⁴⁾,10,12-trien-4-one

(7R,8S)-6,6-bis{(benzenesulfonyl)-2-fluoro-8-(hydroxymethyl)6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-yl}methanol

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