(E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

Base Information

Chemical Name:(E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate
CAS No.:1346679-84-2
Molecular Formula:C₂₃H₂₆O₅
Molecular Weight:382.456
Hs Code.:

Synonyms:(E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

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Chemical Property of (E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

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Technology Process of (E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

There total 8 articles about (E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)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: 83.0%

: C₁₉H₂₀O₄

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: (Z)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 1346679-84-2
(E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

Guidance literature:: In toluene; for 6h; optical yield given as %de; Inert atmosphere; Reflux;
DOI:10.1016/j.tetlet.2011.09.043

Reference yield:

: 123-08-0,65581-83-1
4-hydroxy-benzaldehyde

: (Z)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 1346679-84-2
(E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 60 °C / Inert atmosphere

2.1: toluene / 4 h / Inert atmosphere; Reflux

3.1: AD-mix-α; methanesulfonamide; water / tert-butyl alcohol / 24 h / 0 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.33 h / 0 - 20 °C / Inert atmosphere

5.2: 2 h / 0 - 20 °C / Inert atmosphere

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.67 h / -78 °C / Inert atmosphere

6.2: -78 - 0 °C / Inert atmosphere

7.1: toluene / 6 h / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; oxalyl dichloride; methanesulfonamide; AD-mix-α; water; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.1: Wittig reaction / 3.1: Sharpless dihydroxylation / 6.1: Swern oxidation / 6.2: Swern oxidation / 7.1: Wittig reaction;
DOI:10.1016/j.tetlet.2011.09.043

Reference yield:

: 104315-07-3
(E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate

: (Z)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 1346679-84-2
(E)-ethyl 3-((4S,5S)-5-(4-(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: AD-mix-α; methanesulfonamide; water / tert-butyl alcohol / 24 h / 0 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.33 h / 0 - 20 °C / Inert atmosphere

3.2: 2 h / 0 - 20 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.67 h / -78 °C / Inert atmosphere

4.2: -78 - 0 °C / Inert atmosphere

5.1: toluene / 6 h / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; oxalyl dichloride; methanesulfonamide; AD-mix-α; water; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; 1.1: Sharpless dihydroxylation / 4.1: Swern oxidation / 4.2: Swern oxidation / 5.1: Wittig reaction;
DOI:10.1016/j.tetlet.2011.09.043