(R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

Base Information

Chemical Name:(R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate
CAS No.:1403608-20-7
Molecular Formula:C₂₄H₃₂O₇
Molecular Weight:432.514
Hs Code.:

Synonyms:(R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

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Chemical Property of (R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

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Technology Process of (R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

There total 18 articles about (R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate 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%

: 1403608-19-4
(S,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

: 1403608-20-7
(R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 1h;
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

: 1403608-20-7
(R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

Guidance literature:: Multi-step reaction with 7 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

6.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 1.5 h

7.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; toluene; mineral oil; 4.1: Julia-Kocienski olefination / 4.2: Julia-Kocienski olefination / 6.1: Mitsunobu reaction;
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

: 1403608-20-7
(R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

Guidance literature:: Multi-step reaction with 4 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

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 1.5 h

4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C

With 18-crown-6 ether; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; potassium hexamethylsilazane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; toluene; 1.1: Julia-Kocienski olefination / 1.2: Julia-Kocienski olefination / 3.1: Mitsunobu reaction;
DOI:10.1002/ejoc.201200241