[(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-on-4-yl](phenyl)methyl O-phenyl carbonothioate

Base Information

• Chemical Name: [(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-on-4-yl](phenyl)methyl O-phenyl carbonothioate
• CAS No.: 313548-02-6
• Molecular Formula: C₂₈H₂₆O₆S
• Molecular Weight: 490.577

Synonyms:[(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-on-4-yl](phenyl)methyl O-phenyl carbonothioate

Chemical Property of [(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-on-4-yl](phenyl)methyl O-phenyl carbonothioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-on-4-yl](phenyl)methyl O-phenyl carbonothioate

There total 15 articles about [(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-on-4-yl](phenyl)methyl O-phenyl carbonothioate 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:

(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4-[hydroxy(phenyl)methyl]-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-one (313548-01-5) + phenylcarbonochloridothioate (1005-56-7) → [(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-on-4-yl](phenyl)methyl O-phenyl carbonothioate (313548-02-6)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2005.10.082

Reference yield:

(3R,4R,5R)-3-[(tert-butyl-dimethylsilyl)oxy]-4,5-(isopropylidenedioxy)-1-cyclohexanone (313547-95-4) → [(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-on-4-yl](phenyl)methyl O-phenyl carbonothioate (313548-02-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 53 percent / sodium borohydride / H₂O; tetrahydrofuran / 1 h / 20 °C

2.1: 98 percent / diethyl azodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 3 h / 20 °C

3.1: 100 percent / potassium hydroxide / methanol / 3 h / 20 °C

4.1: 67 percent / diethyl azodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 3 h / 20 °C

5.1: 92 percent / 3-chloroperoxybenzoic acid; sodium hydrogen carbonate / CH₂Cl₂ / 24 h / 20 °C

6.1: soduim borohydride; diphenyl diselenide / ethanol / 1 h / Heating

6.2: 78 percent / hydrogen peroxide / H₂O; ethanol / 1 h / Heating

7.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

8.1: 97 percent / diethylaluminium chloride / hexane; CH₂Cl₂ / 2 h / -78 - 0 °C

9.1: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

10.1: 86 percent / N-bromosuccinimide / CH₂Cl₂ / 1 h / 20 °C

11.1: 98 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

12.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

12.2: tetrahydrofuran / 1 h / -78 °C

13.1: 4-(dimethylamino)pyridine / acetonitrile / 12 h / 20 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; diphenyl diselenide; tetrabutyl ammonium fluoride; diethylaluminium chloride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; 2.1: Mitsunobu reaction / 7.1: Dess-Martin oxidation / 8.1: Diels-Alder reaction;

DOI:10.1016/j.tet.2005.10.082

Reference yield:

(3aR,7R,7aS)-7-hydroxy-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one (74293-60-0) → [(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.02,7.02,10]undecan-3-on-4-yl](phenyl)methyl O-phenyl carbonothioate (313548-02-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 98 percent / imidazole / dimethylformamide / 15 h / 20 °C

2.1: 53 percent / sodium borohydride / H₂O; tetrahydrofuran / 1 h / 20 °C

3.1: 98 percent / diethyl azodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 3 h / 20 °C

4.1: 100 percent / potassium hydroxide / methanol / 3 h / 20 °C

5.1: 67 percent / diethyl azodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 3 h / 20 °C

6.1: 92 percent / 3-chloroperoxybenzoic acid; sodium hydrogen carbonate / CH₂Cl₂ / 24 h / 20 °C

7.1: soduim borohydride; diphenyl diselenide / ethanol / 1 h / Heating

7.2: 78 percent / hydrogen peroxide / H₂O; ethanol / 1 h / Heating

8.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

9.1: 97 percent / diethylaluminium chloride / hexane; CH₂Cl₂ / 2 h / -78 - 0 °C

10.1: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

11.1: 86 percent / N-bromosuccinimide / CH₂Cl₂ / 1 h / 20 °C

12.1: 98 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

13.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

13.2: tetrahydrofuran / 1 h / -78 °C

14.1: 4-(dimethylamino)pyridine / acetonitrile / 12 h / 20 °C

With 1H-imidazole; dmap; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; diphenyl diselenide; tetrabutyl ammonium fluoride; diethylaluminium chloride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Mitsunobu reaction / 8.1: Dess-Martin oxidation / 9.1: Diels-Alder reaction;

DOI:10.1016/j.tet.2005.10.082

upstream raw materials:

(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4-[hydroxy(phenyl)methyl]-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-one

phenylcarbonochloridothioate

(1R,2S,4S,5S,6R,7R,8R,9S,10S)-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-one

cyclopenta-1,3-diene

Downstream raw materials:

(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-7-benzyl-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one

(1R,4S,4aR,5R,6S,7S,8aS)-7-benzyl-5-hydroxy-6,7-O-isopropylidenedioxy-1,4,4a,5,6,7,8,8a-octahydro-endo-1,4-methanonaphthalen-8-one

(1R,5S,6S)-5-benzyl-5,6-O-isopropylidenedioxy-4-oxo-2-cyclohexenyl methanesulfonate

(1R,5S,6S)-5-benzyl-5,6-dihydroxy-4-oxo-2-cyclohexenyl methanesulfonate

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