(2S,3S,6S,7R,10R,E)-7,10-dihydroxy-3,7-dimethyl-12-oxo-2-p-tolyl-oxacyclododec-4-en-6-yl acetate

Base Information

• Chemical Name: (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-3,7-dimethyl-12-oxo-2-p-tolyl-oxacyclododec-4-en-6-yl acetate
• CAS No.: 1446121-97-6
• Molecular Formula: C₂₂H₃₀O₆
• Molecular Weight: 390.477

Synonyms:(2S,3S,6S,7R,10R,E)-7,10-dihydroxy-3,7-dimethyl-12-oxo-2-p-tolyl-oxacyclododec-4-en-6-yl acetate

Chemical Property of (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-3,7-dimethyl-12-oxo-2-p-tolyl-oxacyclododec-4-en-6-yl acetate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-3,7-dimethyl-12-oxo-2-p-tolyl-oxacyclododec-4-en-6-yl acetate

There total 26 articles about (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-3,7-dimethyl-12-oxo-2-p-tolyl-oxacyclododec-4-en-6-yl acetate 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: 94.0%

(4R,7R,8S,11S,12S,E)-4,7,8-trihydroxy-7,11-dimethyl-12-p-tolyl-oxacyclododec-9-en-2-one (1446121-87-4) + acetic anhydride (108-24-7) → (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-3,7-dimethyl-12-oxo-2-p-tolyl-oxacyclododec-4-en-6-yl acetate (1446121-97-6)

Guidance literature:

In pyridine; at -10 ℃; for 6h; regioselective reaction;

DOI:10.1021/ol401458d

Reference yield:

(4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-4-(4-methylpent-3-enyl)-1,3-dioxolane (1446120-09-7) → (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-3,7-dimethyl-12-oxo-2-p-tolyl-oxacyclododec-4-en-6-yl acetate (1446121-97-6)

Guidance literature:

Multi-step reaction with 15 steps

1.1: ozone / dichloromethane / 0.67 h / -78 °C

1.2: 4 h / -78 - 20 °C

2.1: benzene / 8 h / 20 °C

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 4 h / 20 °C

4.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane; toluene / 18 h / -20 °C / Molecular sieve; Inert atmosphere

5.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene; tetrahydrofuran / 8 h / -40 °C

5.2: 1 h / 20 °C

6.1: dmap; 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C

7.1: hydrogen / methanol / 1 h / 20 °C

8.1: potassium carbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

9.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C

9.2: 6 h / -20 °C

10.1: hydrogen fluoride / tetrahydrofuran; pyridine / 8 h / -10 °C

11.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / 4 h / 0 °C

12.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3.17 h / 0 - 20 °C / Inert atmosphere

12.2: 8 h / 20 °C / Inert atmosphere

13.1: pyridinium p-toluenesulfonate / methanol / 4 h / 0 - 50 °C

14.1: Hoveyda-Grubbs catalyst second generation; p-benzoquinone / toluene / 2 h / 100 °C / Inert atmosphere

15.1: pyridine / 6 h / -10 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; Hoveyda-Grubbs catalyst second generation; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diethyl (2S,3S)-tartrate; [bis(acetoxy)iodo]benzene; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; ozone; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; toluene; acetonitrile; benzene; 4.1: |Sharpless Asymmetric Epoxidation / 9.1: |Wittig Olefination / 9.2: |Wittig Olefination / 12.1: |Yamaguchi Lactonization / 12.2: |Yamaguchi Lactonization;

DOI:10.1021/ol401458d

Reference yield:

(E)-ethyl 5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-enoate (1446120-17-7) → (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-3,7-dimethyl-12-oxo-2-p-tolyl-oxacyclododec-4-en-6-yl acetate (1446121-97-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 4 h / 20 °C

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane; toluene / 18 h / -20 °C / Molecular sieve; Inert atmosphere

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene; tetrahydrofuran / 8 h / -40 °C

3.2: 1 h / 20 °C

4.1: dmap; 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C

5.1: hydrogen / methanol / 1 h / 20 °C

6.1: potassium carbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C

7.2: 6 h / -20 °C

8.1: hydrogen fluoride / tetrahydrofuran; pyridine / 8 h / -10 °C

9.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / 4 h / 0 °C

10.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3.17 h / 0 - 20 °C / Inert atmosphere

10.2: 8 h / 20 °C / Inert atmosphere

11.1: pyridinium p-toluenesulfonate / methanol / 4 h / 0 - 50 °C

12.1: Hoveyda-Grubbs catalyst second generation; p-benzoquinone / toluene / 2 h / 100 °C / Inert atmosphere

13.1: pyridine / 6 h / -10 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; Hoveyda-Grubbs catalyst second generation; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diethyl (2S,3S)-tartrate; [bis(acetoxy)iodo]benzene; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; toluene; acetonitrile; 2.1: |Sharpless Asymmetric Epoxidation / 7.1: |Wittig Olefination / 7.2: |Wittig Olefination / 10.1: |Yamaguchi Lactonization / 10.2: |Yamaguchi Lactonization;

DOI:10.1021/ol401458d

upstream raw materials:

(4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-4-(4-methylpent-3-enyl)-1,3-dioxolane

(4R,7R,8S,11S,12S,E)-4,7,8-trihydroxy-7,11-dimethyl-12-p-tolyl-oxacyclododec-9-en-2-one

acetic anhydride

(E)-ethyl 5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-enoate

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