(R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol

Base Information

Chemical Name:(R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol
CAS No.:1403608-10-5
Molecular Formula:C₂₂H₃₂O₅
Molecular Weight:376.493
Hs Code.:

Synonyms:(R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol

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Chemical Property of (R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol

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Technology Process of (R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol

There total 8 articles about (R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-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: 88.0%

: 1403608-18-3
(4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

: 1403608-10-5
(R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1002/ejoc.201200241

Reference yield:

: 866022-02-8
(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

: 1403608-10-5
(R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C

1.2: 2 h / 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / Cooling

4.2: 2 h / 20 °C / Cooling

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

With tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene; mineral oil; 4.1: Julia-Kocienski olefination / 4.2: Julia-Kocienski olefination;
DOI:10.1002/ejoc.201200241

Reference yield:

: 1403608-11-6
(4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

: 1403608-10-5
(R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / Cooling

1.2: 2 h / 20 °C / Cooling

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

With 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; toluene; 1.1: Julia-Kocienski olefination / 1.2: Julia-Kocienski olefination;
DOI:10.1002/ejoc.201200241