(3R,6R,7S)-((1S,2S)-2-methyl-1-p-tolylbut-3-enyl) 3,6,7-trihydroxy-6-methylnon-8-enoate

Base Information

Chemical Name:(3R,6R,7S)-((1S,2S)-2-methyl-1-p-tolylbut-3-enyl) 3,6,7-trihydroxy-6-methylnon-8-enoate
CAS No.:1446121-75-0
Molecular Formula:C₂₂H₃₂O₅
Molecular Weight:376.493
Hs Code.:

Synonyms:(3R,6R,7S)-((1S,2S)-2-methyl-1-p-tolylbut-3-enyl) 3,6,7-trihydroxy-6-methylnon-8-enoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,6R,7S)-((1S,2S)-2-methyl-1-p-tolylbut-3-enyl) 3,6,7-trihydroxy-6-methylnon-8-enoate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (3R,6R,7S)-((1S,2S)-2-methyl-1-p-tolylbut-3-enyl) 3,6,7-trihydroxy-6-methylnon-8-enoate

There total 24 articles about (3R,6R,7S)-((1S,2S)-2-methyl-1-p-tolylbut-3-enyl) 3,6,7-trihydroxy-6-methylnon-8-enoate 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: 90.0%

: 1446121-63-6
(R)-((1S,2S)-2-methyl-1-p-tolylbut-3-enyl)-3-(tert-butyldimethylsilyl-oxy)-5-((4R,5S)-2,2,4-trimethyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate

: 1446121-75-0
(3R,6R,7S)-((1S,2S)-2-methyl-1-p-tolylbut-3-enyl) 3,6,7-trihydroxy-6-methylnon-8-enoate

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; at 0 - 50 ℃; for 4h;
DOI:10.1021/ol401458d

Reference yield:

: 1446120-09-7
(4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-4-(4-methylpent-3-enyl)-1,3-dioxolane

: 1446121-75-0
(3R,6R,7S)-((1S,2S)-2-methyl-1-p-tolylbut-3-enyl) 3,6,7-trihydroxy-6-methylnon-8-enoate

Guidance literature:: Multi-step reaction with 13 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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; 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; 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:

: 1446120-25-7
((2R,3R)-3-(2-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)ethyl)oxiran-2-yl)methanol

: 1446121-75-0
(3R,6R,7S)-((1S,2S)-2-methyl-1-p-tolylbut-3-enyl) 3,6,7-trihydroxy-6-methylnon-8-enoate

Guidance literature:: Multi-step reaction with 9 steps

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

1.2: 1 h / 20 °C

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

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

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

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

5.2: 6 h / -20 °C

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

7.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / 4 h / 0 °C

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

8.2: 8 h / 20 °C / Inert atmosphere

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

With 1H-imidazole; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; toluene; acetonitrile; 5.1: |Wittig Olefination / 5.2: |Wittig Olefination / 8.1: |Yamaguchi Lactonization / 8.2: |Yamaguchi Lactonization;
DOI:10.1021/ol401458d