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

Base Information

Chemical Name:(E)-ethyl 5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-enoate
CAS No.:1446120-17-7
Molecular Formula:C₂₁H₃₀O₅
Molecular Weight:362.466
Hs Code.:

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

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

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

There total 6 articles about (E)-ethyl 5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-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: 94.0%

: 1446120-13-3
3-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)propanal

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1446120-17-7
(E)-ethyl 5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-enoate

Guidance literature:: In benzene; at 20 ℃; for 8h;
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

: 1446120-17-7
(E)-ethyl 5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 4 h / -78 - 20 °C

2.1: benzene / 8 h / 20 °C

With ozone; In dichloromethane; benzene;
DOI:10.1021/ol401458d

Reference yield:

: 106-24-1
Geraniol

: 1446120-17-7
(E)-ethyl 5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: diethyl tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; toluene / 6 h / -20 °C / Molecular sieve; Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere

2.2: 19 h / 0 - 20 °C / Inert atmosphere

3.1: perchloric acid / tetrahydrofuran; water / 13 h / 0 - 20 °C

4.1: camphorsulfonic acid / dichloromethane / 0.5 h / 20 °C

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

5.2: 4 h / -78 - 20 °C

6.1: benzene / 8 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; perchloric acid; diethyl tartrate; sodium hydride; ozone; In tetrahydrofuran; dichloromethane; water; toluene; mineral oil; benzene; 1.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1021/ol401458d