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

Base Information

Chemical Name:(E)-5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol
CAS No.:1446120-21-3
Molecular Formula:C₁₉H₂₈O₄
Molecular Weight:320.429
Hs Code.:

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

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

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

There total 7 articles about (E)-5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol 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: 78.0%

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

: 1446120-21-3
(E)-5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; toluene; at 20 ℃; 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

: 1446120-21-3
(E)-5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 3 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

With diisobutylaluminium hydride; ozone; In dichloromethane; toluene; benzene;
DOI:10.1021/ol401458d

Reference yield:

: 106-24-1
Geraniol

: 1446120-21-3
(E)-5-((4R,5S)-5-(benzyloxymethyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 7 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

7.1: diisobutylaluminium hydride / dichloromethane; toluene / 4 h / 20 °C

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