(1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyl acrylate

Base Information

Chemical Name:(1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyl acrylate
CAS No.:1308247-25-7
Molecular Formula:C₂₀H₂₆O₆
Molecular Weight:362.423
Hs Code.:

Synonyms:(1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyl acrylate

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Chemical Property of (1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyl acrylate

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Technology Process of (1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyl acrylate

There total 8 articles about (1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyl acrylate 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: 86.0%

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

: (1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-en-1-ol

: 1308247-25-7
(1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyl acrylate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/j.tet.2011.03.107

Reference yield:

: 879572-98-2
ethyl (2R,3R)-3,4-O-isopropylidene-2-[(tert-butyldimethylsilyl)oxy]-3,4-dihydroxybutanoate

: 1308247-25-7
(1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyl acrylate

Guidance literature:: Multi-step reaction with 7 steps

1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C

2: tetrahydrofuran / 3.33 h / -78 - 20 °C

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 20 °C

4: potassium tri-sec-butyl-borohydride / tetrahydrofuran; toluene / 6 h / -78 - -40 °C

5: sodium hydride / tetrahydrofuran / 0 - 20 °C

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

7: triethylamine / dichloromethane / 0 - 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; potassium tri-sec-butyl-borohydride; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1016/j.tet.2011.03.107

Reference yield:

: 1175536-43-2
(1S,2S)-1-(tert-butyldimethylsilyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-2-ol

: 1308247-25-7
(1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyl acrylate

Guidance literature:: Multi-step reaction with 5 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 20 °C

2: potassium tri-sec-butyl-borohydride / tetrahydrofuran; toluene / 6 h / -78 - -40 °C

3: sodium hydride / tetrahydrofuran / 0 - 20 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

5: triethylamine / dichloromethane / 0 - 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; potassium tri-sec-butyl-borohydride; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1016/j.tet.2011.03.107