(4R,E)-4-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-2-hexene

Base Information

Chemical Name:(4R,E)-4-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-2-hexene
CAS No.:1579954-61-2
Molecular Formula:C₂₄H₄₀O₄Si
Molecular Weight:420.665
Hs Code.:

Synonyms:(4R,E)-4-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-2-hexene

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Chemical Property of (4R,E)-4-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-2-hexene

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Technology Process of (4R,E)-4-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-2-hexene

There total 7 articles about (4R,E)-4-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-2-hexene 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%

: 1579954-60-1
6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-hex-2-en-4-ol

: 100-39-0
benzyl bromide

: 1579954-61-2
(4R,E)-4-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-2-hexene

Guidance literature:: 6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-hex-2-en-4-ol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 1h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 0 - 55 ℃; for 10h;
DOI:10.3987/COM-13-12896

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1579954-61-2
(4R,E)-4-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-2-hexene

Guidance literature:: Multi-step reaction with 7 steps

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

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1 h / 20 °C

5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; toluene / 1 h / 0 - 20 °C / Inert atmosphere

6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 7 h / -78 - -35 °C / Inert atmosphere

7.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C

7.2: 10 h / 0 - 55 °C

With n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; sodium hydride; dimethyl sulfoxide; sodium bis(2-methoxyethoxy)aluminium dihydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene; mineral oil; 2.1: |Swern Oxidation;
DOI:10.3987/COM-13-12896

Reference yield:

: 73842-99-6
3-tert-butyldimethylsilyloxy-1-propanol

: 1579954-61-2
(4R,E)-4-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-1-(tetrahydropyran-2-yloxy)-2-hexene

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1 h / 20 °C

4.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; toluene / 1 h / 0 - 20 °C / Inert atmosphere

5.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 7 h / -78 - -35 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C

6.2: 10 h / 0 - 55 °C

With n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; sodium hydride; dimethyl sulfoxide; sodium bis(2-methoxyethoxy)aluminium dihydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene; mineral oil; 1.1: |Swern Oxidation;
DOI:10.3987/COM-13-12896