(1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-yl prop-2-enoate

Base Information

Chemical Name:(1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-yl prop-2-enoate
CAS No.:1006371-17-0
Molecular Formula:C₁₈H₂₂O₄
Molecular Weight:302.37
Hs Code.:

Synonyms:(1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-yl prop-2-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 (1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-yl prop-2-enoate

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Technology Process of (1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-yl prop-2-enoate

There total 7 articles about (1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-yl prop-2-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: 75.0%

: 814-68-6,25189-84-8
acryloyl chloride

: 474958-87-7
(1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-ol

: 1006371-17-0
(1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-yl prop-2-enoate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1055/s-2007-990866

Reference yield:

: 153481-85-7
(4R,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolane-4-carbaldehyde

: 1006371-17-0
(1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-yl prop-2-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

1.2: 6 h / -78 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere

3.1: 1H-imidazole; dmap / dichloromethane / 4 h / 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere

5.1: potassium tert-butylate / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 5.1: |Wittig Olefination;
DOI:10.1002/hlca.201200368

Reference yield:

: (4R)-4-benzyl-3-{(3R)-3-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-3-hydroxypropanoyl}-1,3-oxazolidin-2-one

: 1006371-17-0
(1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-yl prop-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere

2: 1H-imidazole; dmap / dichloromethane / 4 h / 20 °C / Inert atmosphere

3: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere

4: potassium tert-butylate / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

6: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 4: |Wittig Olefination;
DOI:10.1002/hlca.201200368